Aryl substituted bicyclic compounds as herbicides

ABSTRACT

Also disclosed are compositions containing the compounds of Formula 1 and methods for controlling undesired vegetation comprising contacting the undesired vegetation or its environment with an effective amount of a compound or a composition of the invention.

FIELD OF THE INVENTION

This invention relates to certain bicyclic carboxamides, their N-oxides,salts and compositions, and methods of their use for controllingundesirable vegetation.

BACKGROUND OF THE INVENTION

The control of undesired vegetation is extremely important in achievinghigh crop efficiency. Achievement of selective control of the growth ofweeds especially in such useful crops as rice, soybean, sugar beet,maize, potato, wheat, barley, tomato and plantation crops, among others,is very desirable. Unchecked weed growth in such useful crops can causesignificant reduction in productivity and thereby result in increasedcosts to the consumer. The control of undesired vegetation in noncropareas is also important. Many products are commercially available forthese purposes, but the need continues for new compounds that are moreeffective, less costly, less toxic, environmentally safer or havedifferent sites of action.

SUMMARY OF THE INVENTION

This invention is directed to a compound of Formula 1 (including allstereoisomers), including N-oxides and salts thereof, agriculturalcompositions containing them and their use as herbicides:

wherein

-   -   Q¹ is a phenyl or benzyl ring or a naphthalenyl ring system,        each ring or ring system optionally substituted with up to 5        substituents independently selected from R⁹; or a 5- to        6-membered fully unsaturated heterocyclic ring or an 8- to        10-membered heteroaromatic bicyclic ring system, each ring or        ring system containing ring members selected from carbon atoms        and 1 to 4 heteroatoms independently selected from up to 2 O, up        to 2 S and up to 4 N atoms, wherein up to 3 carbon ring members        are independently selected from C(═O) and C(═S), and the sulfur        atom ring members are independently selected from        S(═O)_(u)(═NR⁸)_(v), each ring or ring system optionally        substituted with up to 5 substituents independently selected        from R⁹ on carbon atom ring members and selected from R¹⁰ on        nitrogen atom ring members;    -   Q² is a phenyl ring or a naphthalenyl ring system, each ring or        ring system optionally substituted with up to 5 substituents        independently selected from R¹¹; or a 5- to 6-membered fully        unsaturated heterocyclic ring or an 8- to 10-membered        heteroaromatic bicyclic ring system, each ring or ring system        containing ring members selected from carbon atoms and 1 to 4        heteroatoms independently selected from up to 2 O, up to 2 S and        up to 4 N atoms, wherein up to 3 carbon ring members are        independently selected from C(═O) and C(═S), and the sulfur atom        ring members are independently selected from        S(═O)_(u)(═NR⁸)_(v), each ring or ring system optionally        substituted with up to 5 substituents independently selected        from R¹¹ on carbon atom ring members and selected from R¹² on        nitrogen atom ring members;    -   R¹ and R² are each independently H, halogen, hydroxy or C₁-C₄        alkyl;    -   Y is O, S or NR¹⁵;    -   A is a saturated, partially unsaturated or fully unsaturated        chain containing 2 to 4 atoms selected from up to 4 carbon, up        to 1 O, up to 1 S and up to 2 N atoms, wherein up to 2 carbon        members are independently selected from C(═O) and C(═S) and the        sulfur atom member is selected from S(═O)_(u)(═NR⁸)_(v); the        said chain optionally substituted with up to 5 substituents        independently selected from R³ on carbon atoms and R⁴ on        nitrogen atoms;    -   each R³ is independently halogen, cyano, hydroxy, —CO₂H, C₁-C₄        alkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy, C₁-C₄ alkylthio, C₁-C₄        haloalkoxy, C₂-C₄ alkoxyalkyl, C₂-C₄ alkylcarbonyl, C₂-C₄        alkoxycarbonyl, C₃-C₆ cycloalkyl or C₄-C₆ cycloalkylalkyl; or    -   two R³ are taken together with the carbon atom(s) to which they        are bonded to form a C₃-C₇ cycloalkyl ring;    -   each R⁴ is independently cyano, C₁-C₄ alkyl, C₁-C₄ haloalkyl,        C₁-C₄ alkoxy, C₂-C₄ alkylcarbonyl, C₂-C₄ alkoxycarbonyl or C₃-C₆        cycloalkyl;    -   J is —CR⁵R⁶— or —CR⁵R⁶—CR^(5a)R^(6a)— wherein the —CR⁵R⁶— moiety        is directly connected to N;    -   R⁵ and R⁶ are each independently H, halogen, hydroxy, C₁-C₄        alkyl or C₁-C₄ alkoxy; or    -   R⁵ and R⁶ are taken together with the carbon atom to which they        are bonded to form a C₃-C₇ cycloalkyl ring;    -   R^(5a) and R^(6a) are each independently H, halogen or C₁-C₄        alkyl; or    -   R^(5a) and R^(6a) are taken together with the carbon atom to        which they are bonded to form a C₃-C₇ cycloalkyl ring;    -   R⁷ is H, hydroxy, amino, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆        alkenyl, C₃-C₆ alkynyl, C₂-C₈ alkoxyalkyl, C₂-C₈        haloalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl,        C₂-C₈ alkylsulfonylalkyl, C₂-C₈ alkylcarbonyl, C₂-C₈        haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, C₂-C₈        alkoxycarbonyl, C₂-C₈ haloalkoxycarbonyl, C₄-C₁₀        cycloalkoxycarbonyl, C₂-C₈ alkylaminocarbonyl, C₃-C₁₀        dialkylaminocarbonyl, C₄-C₁₀ cycloalkylaminocarbonyl, C₁-C₆        alkoxy, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₃-C₈        cycloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl,        C₃-C₈ cycloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆        haloalkylsulfonyl, C₃-C₈ cycloalkylsulfonyl, C₁-C₆        alkylaminosulfonyl, C₂-C₈ dialkylaminosulfonyl, C₃-C₁₀        trialkylsilyl or G¹;    -   each R⁸ is independently H, cyano, C₂-C₃ alkylcarbonyl or C₂-C₃        haloalkylcarbonyl;    -   each R⁹ is independently halogen, cyano, nitro, C₁-C₈ alkyl,        C₁-C₄ cyanoalkyl, C₁-C₄ cyanoalkoxy, C₁-C₈ haloalkyl, C₁-C₈        nitroalkyl, C₂-C₈ alkenyl, C₂-C₈ haloalkenyl, C₂-C₈        nitroalkenyl, C₂-C₈ alkynyl, C₂-C₈ haloalkynyl, C₄-C₁₀        cycloalkylalkyl, C₄-C₁₀ halocycloalkylalkyl, C₅-C₁₂        alkylcycloalkylalkyl, C₅-C₁₂ cycloalkylalkenyl, C₅-C₁₂        cycloalkylalkynyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl,        C₄-C₁₀ alkylcycloalkyl, C₆-C₁₂ cycloalkylcycloalkyl, C₃-C₈        cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₂-C₈        haloalkoxyalkyl, C₃-C₈ haloalkoxyalkoxy, C₁-C₄ hydroxyalkyl,        C₄-C₁₀ cycloalkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈        alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈        alkylsulfonylalkyl, C₂-C₈ alkylaminoalkyl, C₂-C₈        haloalkylaminoalkyl, C₄-C₁₀ cycloalkylaminoalkyl, C₃-C₁₀        dialkylaminoalkyl, —CHO, C₂-C₈ alkylcarbonyl, C₂-C₈        haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, —C(═O)OH, C₂-C₈        alkoxycarbonyl, C₂-C₈ haloalkoxycarbonyl, C₄-C₁₀        cycloalkoxycarbonyl, C₅-C₁₂ cycloalkylalkoxycarbonyl, —C(═O)NH₂,        C₂-C₈ alkylaminocarbonyl, C₄-C₁₀ cycloalkylaminocarbonyl, C₃-C₁₀        dialkylaminocarbonyl, C₁-C₈ alkoxy, C₁-C₈ haloalkoxy, C₂-C₈        alkoxyalkoxy, C₂-C₈ alkenyloxy, C₂-C₈ haloalkenyloxy, C₂-C₈        haloalkoxyhaloalkoxy, C₃-C₈ alkynyloxy, C₃-C₈ haloalkynyloxy,        C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₄-C₁₀        cycloalkylalkoxy, C₃-C₁₀ alkylcarbonylalkoxy, C₂-C₈        alkylcarbonyloxy, C₂-C₈ haloalkylcarbonyloxy, C₄-C₁₀        cycloalkylcarbonyloxy, C₁-C₈ alkylsulfonyloxy, C₁-C₈        haloalkylsulfonyloxy, C₁-C₈ alkylthio, C₁-C₈ haloalkylthio,        C₃-C₈ cycloalkylthio, C₁-C₈ alkylsulfinyl, C₁-C₈        haloalkylsulfinyl, C₁-C₈ alkyl sulfonyl, C₁-C₈        haloalkylsulfonyl, C₃-C₈ cycloalkylsulfonyl, formylamino, C₂-C₈        alkylcarbonylamino, C₂-C₈ haloalkylcarbonylamino, C₂-C₈        alkoxycarbonylamino, C₁-C₆ alkylsulfonylamino, C₁-C₆        haloalkylsulfonylamino, —SF₅, —SCN, SO₂NH₂, C₃-C₁₂        trialkylsilyl, C₄-C₁₂ trialkylsilylalkyl, C₄-C₁₂        trialkylsilylalkoxy or G²;    -   each R¹¹ is independently halogen, cyano, nitro, C₁-C₈ alkyl,        C₁-C₄ cyanoalkyl, C₁-C₄ cyanoalkoxy, C₁-C₈ haloalkyl, C₁-C₈        nitroalkyl, C₂-C₈ alkenyl, C₂-C₈ haloalkenyl, C₂-C₈        nitroalkenyl, C₂-C₈ alkynyl, C₂-C₈ haloalkynyl, C₄-C₁₀        cycloalkylalkyl, C₄-C₁₀ halocycloalkylalkyl, C₅-C₁₂        alkylcycloalkylalkyl, C₅-C₁₂ cycloalkylalkenyl, C₅-C₁₂        cycloalkylalkynyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl,        C₄-C₁₀ alkylcycloalkyl, C₆-C₁₂ cycloalkylcycloalkyl, C₃-C₈        cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₂-C₈        haloalkoxyalkyl, C₃-C₈ haloalkoxyalkoxy, C₁-C₄ hydroxyalkyl,        C₄-C₁₀ cycloalkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈        alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈        alkylsulfonylalkyl, C₂-C₈ alkylaminoalkyl, C₂-C₈        haloalkylaminoalkyl, C₄-C₁₀ cycloalkylaminoalkyl, C₃-C₁₀        dialkylaminoalkyl, —CHO, C₂-C₈ alkylcarbonyl, C₂-C₈        haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, —C(═O)OH, C₂-C₈        alkoxycarbonyl, C₂-C₈ haloalkoxycarbonyl, C₄-C₁₀        cycloalkoxycarbonyl, C₅-C₁₂ cycloalkylalkoxycarbonyl, —C(═O)NH₂,        C₂-C₈ alkylaminocarbonyl, C₄-C₁₀ cycloalkylaminocarbonyl, C₃-C₁₀        dialkylaminocarbonyl, C₁-C₈ alkoxy, C₁-C₈ haloalkoxy, C₂-C₈        alkoxyalkoxy, C₂-C₈ alkenyloxy, C₂-C₈ haloalkenyloxy, C₂-C₈        haloalkoxyhaloalkoxy, C₃-C₈ alkynyloxy, C₃-C₈ haloalkynyloxy,        C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₄-C₁₀        cycloalkylalkoxy, C₃-C₁₀ alkylcarbonylalkoxy, C₂-C₈        alkylcarbonyloxy, C₂-C₈ haloalkylcarbonyloxy, C₄-C₁₀        cycloalkylcarbonyloxy, C₁-C₈ alkylsulfonyloxy, C₁-C₈        haloalkylsulfonyloxy, C₁-C₈ alkylthio, C₁-C₈ haloalkylthio,        C₃-C₈ cycloalkylthio, C₁-C₈ alkylsulfinyl, C₁-C₈        haloalkylsulfinyl, C₁-C₈ alkyl sulfonyl, C₁-C₈        haloalkylsulfonyl, C₃-C₈ cycloalkylsulfonyl, formylamino, C₂-C₈        alkylcarbonylamino, C₂-C₈ haloalkylcarbonylamino, C₂-C₈        alkoxycarbonylamino, C₁-C₆ alkylsulfonylamino, C₁-C₆        haloalkylsulfonylamino, —SF₅, —SCN, SO₂NH₂, C₃-C₁₂        trialkylsilyl, C₄-C₁₂ trialkylsilylalkyl, C₄-C₁₂        trialkylsilylalkoxy or G³;    -   each R¹⁰ and R¹² is independently cyano, C₁-C₃ alkyl, C₂-C₃        alkenyl, C₂-C₃ alkynyl, C₃-C₆ cycloalkyl, C₂-C₃ alkoxyalkyl,        C₁-C₃ alkoxy, C₂-C₃ alkylcarbonyl, C₂-C₃ alkoxycarbonyl, C₂-C₃        alkylaminoalkyl or C₃-C₄ dialkylaminoalkyl;    -   R¹⁵ is H, cyano, C₁-C₄ alkyl, C₁-C₄ haloalkyl, —(C═O)CH₃ or        —(C═O)CF₃;    -   each G¹ is independently phenyl, phenylmethyl (i.e. benzyl),        pyridinylmethyl, pyridinyloxy, phenylcarbonyl (i.e. benzoyl),        phenoxy, phenylethynyl, phenylsulfonyl, phenylcarbonyl(C₁-C₄        alkyl); or a 5- or 6-membered heteroaromatic ring, each        optionally substituted on ring members with up to 5 substituents        independently selected from R¹³;    -   each G² is independently phenyl, phenylmethyl (i.e. benzyl),        pyridinylmethyl, phenylcarbonyl (i.e. benzoyl),        phenylcarbonylalkyl, phenoxy, phenylethynyl, phenylsulfonyl or        pyridyloxy; or a 5- or 6-membered heteroaromatic ring, each        optionally substituted on ring members with up to 5 substituents        independently selected from R¹⁴; or R¹⁶ON═CR¹⁷—, (R¹⁸)₂C═NO—,        (R¹⁹)₂NN═CR¹⁷—, (R¹⁸)₂C═NNR²⁰—, R²¹N═CR¹⁷—, (R¹⁸)₂C═N—,        R²²ON═CR¹⁷C(R²³)₂— or (R¹⁸)₂C═NOC(R²³)₂—, wherein the free bond        projecting to the right indicates the connecting point to Q¹;    -   each G³ is independently phenyl, phenylmethyl (i.e. benzyl),        pyridinylmethyl, phenylcarbonyl (i.e. benzoyl),        phenylcarbonylalkyl, phenoxy, phenylethynyl, phenylsulfonyl or        pyridyloxy; or a 5- or 6-membered heteroaromatic ring, each        optionally substituted on ring members with up to 5 substituents        independently selected from R¹⁵;    -   each R¹³, R¹⁴ and R¹⁵ is independently halogen, cyano, hydroxy,        amino, nitro, —CHO, —C(═O)OH, —C(═O)NH₂, —SO₂NH₂, C₁-C₆ alkyl,        C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₂-C₈        alkylcarbonyl, C₂-C₈ haloalkylcarbonyl, C₂-C₈ alkoxycarbonyl,        C₄-C₁₀ cycloalkoxycarbonyl, C₅-C₁₂ cycloalkylalkoxycarbonyl,        C₂-C₈ alkylaminocarbonyl, C₃-C₁₀ dialkylaminocarbonyl, C₁-C₆        alkoxy, C₁-C₆ haloalkoxy, C₂-C₈ alkylcarbonyloxy, C₁-C₆        alkylthio, C₁-C₆ haloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆        haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl,        C₁-C₆ alkylaminosulfonyl, C₂-C₈ dialkylaminosulfonyl, C₃-C₁₀        trialkylsilyl, C₁-C₆ alkylamino, C₂-C₈ dialkylamino, C₂-C₈        alkylcarbonylamino or C₁-C₆ alkylsulfonylamino;    -   each R¹⁶ is independently H, C₁-C₆ alkyl, C₃-C₈ cycloalkyl,        C₄-C₈ cycloalkylalkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₃-C₆        alkynyl, C₂-C₈ alkoxyalkyl, C₂-C₈ haloalkoxyalkyl, C₂-C₈        alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈        alkylsulfonylalkyl, C₂-C₈ alkylcarbonyl, C₂-C₈        haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, C₂-C₈        alkoxycarbonyl, C₂-C₈ haloalkoxycarbonyl, C₄-C₁₀        cycloalkoxycarbonyl, C₂-C₈ alkylaminocarbonyl, C₃-C₁₀        dialkylaminocarbonyl, C₄-C₁₀ cycloalkylaminocarbonyl, C₁-C₆        alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₃-C₈        cycloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆        haloalkylsulfonyl, C₃-C₈ cycloalkylsulfonyl, C₁-C₆        alkylaminosulfonyl, C₂-C₈ dialkylaminosulfonyl, C₃-C₁₀        trialkylsilyl or G¹;    -   each R¹⁷ is independently H, C₁-C₆ alkyl, C₃-C₈ cycloalkyl,        C₄-C₈ cycloalkylalkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₃-C₆        alkynyl, C₂-C₈ alkoxyalkyl, C₂-C₈ haloalkoxyalkyl, C₂-C₈        alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈        alkylsulfonylalkyl, C₁-C₆ alkoxy, C₁-C₆ alkylthio, C₁-C₆        haloalkylthio, C₃-C₈ cycloalkylthio, C₃-C₁₀ trialkylsilyl or G¹;    -   each R¹⁸ is independently H, hydroxy, C₁-C₆ alkyl, C₃-C₈        cycloalkyl, C₄-C₈ cycloalkylalkyl, C₁-C₆ haloalkyl, C₂-C₆        alkenyl, C₃-C₆ alkynyl, C₂-C₈ alkoxyalkyl, C₂-C₈        haloalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl,        C₂-C₈ alkylsulfonylalkyl, C₂-C₈ alkylcarbonyl, C₂-C₈        haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, C₂-C₈        alkoxycarbonyl, C₂-C₈ haloalkoxycarbonyl, C₄-C₁₀        cycloalkoxycarbonyl, C₂-C₈ alkylaminocarbonyl, C₃-C₁₀        dialkylaminocarbonyl, C₄-C₁₀ cycloalkylaminocarbonyl, C₁-C₆        alkoxy, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₃-C₈        cycloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl,        C₃-C₈ cycloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆        haloalkylsulfonyl, C₃-C₈ cycloalkylsulfonyl, C₁-C₆        alkylaminosulfonyl, C₂-C₈ dialkylaminosulfonyl, C₃-C₁₀        trialkylsilyl or G¹;    -   each R¹⁹ is independently H, C₁-C₆ alkyl, C₃-C₈ cycloalkyl,        C₄-C₈ cycloalkylalkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₃-C₆        alkynyl, C₂-C₈ alkoxyalkyl, C₂-C₈ haloalkoxyalkyl, C₂-C₈        alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈        alkylsulfonylalkyl, C₂-C₈ alkylcarbonyl, C₂-C₈        haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, C₂-C₈        alkoxycarbonyl, C₂-C₈ haloalkoxycarbonyl, C₄-C₁₀        cycloalkoxycarbonyl, C₂-C₈ alkylaminocarbonyl, C₃-C₁₀        dialkylaminocarbonyl, C₄-C₁₀ cycloalkylaminocarbonyl, C₁-C₆        alkoxy, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₃-C₈        cycloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆        haloalkylsulfonyl, C₃-C₈ cycloalkylsulfonyl, C₁-C₆        alkylaminosulfonyl, C₂-C₈ dialkylaminosulfonyl, C₃-C₁₀        trialkylsilyl or G¹;    -   each R²⁰ is independently H, C₁-C₆ alkyl, C₃-C₈ cycloalkyl,        C₄-C₈ cycloalkylalkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₃-C₆        alkynyl, C₂-C₈ alkoxyalkyl, C₂-C₈ haloalkoxyalkyl, C₂-C₈        alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈        alkylsulfonylalkyl, C₁-C₆ alkoxyC₃-C₁₀ trialkylsilyl or G¹;    -   each R²¹ is independently H, hydroxy, amino, C₁-C₆ alkyl, C₃-C₈        cycloalkyl, C₄-C₈ cycloalkylalkyl, C₁-C₆ haloalkyl, C₂-C₆        alkenyl, C₃-C₆ alkynyl, C₂-C₈ alkoxyalkyl, C₂-C₈        haloalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl,        C₂-C₈ alkylsulfonylalkyl, C₂-C₈ alkylcarbonyl, C₂-C₈        haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, C₂-C₈        alkoxycarbonyl, C₂-C₈ haloalkoxycarbonyl, C₄-C₁₀        cycloalkoxycarbonyl, C₂-C₈ alkylaminocarbonyl, C₃-C₁₀        dialkylaminocarbonyl, C₄-C₁₀ cycloalkylaminocarbonyl, C₁-C₆        alkoxy, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₃-C₈        cycloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆        haloalkylsulfonyl, C₃-C₈ cycloalkylsulfonyl, C₁-C₆        alkylaminosulfonyl, C₂-C₈ dialkylaminosulfonyl, C₃-C₁₀        trialkylsilyl or G¹;    -   each R²² is independently H, C₁-C₄ alkyl, C₃-C₈ cycloalkyl,        C₄-C₈ cycloalkylalkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy, C₁-C₄        haloalkoxy, C₂-C₄ alkoxyalkyl, C₂-C₄ alkylcarbonyl, C₂-C₄        alkoxycarbonyl or C₃-C₆ cycloalkyl;    -   each R²³ is independently H, halogen, cyano, hydroxy, C₁-C₄        alkyl, C₃-C₈ cycloalkyl, C₄-C₈ cycloalkylalkyl, C₁-C₄ haloalkyl,        C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₂-C₄ alkoxyalkyl, C₂-C₄        alkylcarbonyl, C₂-C₄ alkoxycarbonyl or C₃-C₆ cycloalkyl; and    -   each u and v are independently 0, 1 or 2 in each instance of        S(═O)_(u)(═NR⁸)_(v), provided that the sum of u and v is 0, 1 or        2; and provided the compound is other than a compound of Formula        1 wherein Q¹ is Ph(3-CF₃); Q² is Ph(2-F); R¹ is H; R² is H; Y is        O; A is —CH₂CH₂—; J is —CR⁵R⁶—; R⁵ is H; R⁶ is H; and R⁷ is H.

More particularly, this invention pertains to a compound of Formula 1(including all stereoisomers), an N-oxide or a salt thereof. Thisinvention also relates to a herbicidal composition comprising a compoundof the invention (i.e. in a herbicidally effective amount) and at leastone component selected from the group consisting of surfactants, soliddiluents and liquid diluents. This invention further relates to a methodfor controlling the growth of undesired vegetation comprising contactingthe vegetation or its environment with a herbicidally effective amountof a compound of the invention (e.g., as a composition describedherein).

This invention also includes a herbicidal mixture comprising (a) acompound selected from Formula 1, N-oxides, and salts thereof, and (b)at least one additional active ingredient selected from (b1) through(b16); and salts of compounds of (b1) through (b16), as described below.

DETAILS OF THE INVENTION

As used herein, the terms “comprises,” “comprising,” “includes,”“including,” “has,” “having,” “contains”, “containing,” “characterizedby” or any other variation thereof, are intended to cover anon-exclusive inclusion, subject to any limitation explicitly indicated.For example, a composition, mixture, process or method that comprises alist of elements is not necessarily limited to only those elements butmay include other elements not expressly listed or inherent to suchcomposition, mixture, process or method.

The transitional phrase “consisting of” excludes any element, step, oringredient not specified. If in the claim, such would close the claim tothe inclusion of materials other than those recited except forimpurities ordinarily associated therewith. When the phrase “consistingof” appears in a clause of the body of a claim, rather than immediatelyfollowing the preamble, it limits only the element set forth in thatclause; other elements are not excluded from the claim as a whole.

The transitional phrase “consisting essentially of” is used to define acomposition or method that includes materials, steps, features,components, or elements, in addition to those literally disclosed,provided that these additional materials, steps, features, components,or elements do not materially affect the basic and novelcharacteristic(s) of the claimed invention. The term “consistingessentially of” occupies a middle ground between “comprising” and“consisting of”.

Where applicants have defined an invention or a portion thereof with anopen-ended term such as “comprising,” it should be readily understoodthat (unless otherwise stated) the description should be interpreted toalso describe such an invention using the terms “consisting essentiallyof” or “consisting of.”

Further, unless expressly stated to the contrary, “or” refers to aninclusive or and not to an exclusive or. For example, a condition A or Bis satisfied by any one of the following: A is true (or present) and Bis false (or not present), A is false (or not present) and B is true (orpresent), and both A and B are true (or present).

Also, the indefinite articles “a” and “an” preceding an element orcomponent of the invention are intended to be nonrestrictive regardingthe number of instances (i.e. occurrences) of the element or component.Therefore “a” or “an” should be read to include one or at least one, andthe singular word form of the element or component also includes theplural unless the number is obviously meant to be singular.

As referred to herein, the term “seedling”, used either alone or in acombination of words means a young plant developing from the embryo of aseed.

As referred to herein, the term “broadleaf” used either alone or inwords such as “broadleaf weed” means dicot or dicotyledon, a term usedto describe a group of angiosperms characterized by embryos having twocotyledons.

As used herein, the term “alkylating agent” refers to a chemicalcompound in which a carbon-containing radical is bound through a carbonatom to a leaving group such as halide or sulfonate, which isdisplaceable by bonding of a nucleophile to said carbon atom. Unlessotherwise indicated, the term “alkylating” does not limit thecarbon-containing radical to alkyl; the carbon-containing radicals inalkylating agents include the variety of carbon-bound substituentradicals specified for (R⁹ and R¹¹). The term “directly connected” means“connected” or “bonded”.

In the above recitations, the term “alkyl”, used either alone or incompound words such as “alkylthio” or “haloalkyl” includesstraight-chain or branched alkyl, such as, methyl, ethyl, n-propyl,i-propyl, or the different butyl, pentyl or hexyl isomers. “Alkenyl”includes straight-chain or branched alkenes such as ethenyl, 1-propenyl,2-propenyl, and the different butenyl, pentenyl and hexenyl isomers.“Alkenyl” also includes polyenes such as 1,2-propadienyl and2,4-hexadienyl. “Alkynyl” includes straight-chain or branched alkynessuch as ethynyl, 1-propynyl, 2-propynyl and the different butynyl,pentynyl and hexynyl isomers. “Alkynyl” can also include moietiescomprised of multiple triple bonds such as 2,5-hexadiynyl.

“Alkoxy” includes, for example, methoxy, ethoxy, n-propyloxy,isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers.“Alkoxyalkyl” denotes alkoxy substitution on alkyl. Examples of“alkoxyalkyl” include CH₃OCH₂, CH₃OCH₂CH₂, CH₃CH₂OCH₂, CH₃CH₂CH₂CH₂OCH₂and CH₃CH₂OCH₂CH₂. “Alkoxyalkoxy” denotes alkoxy substitution on alkoxy.“Alkoxyalkoxyalkyl” denotes alkoxy substitution on an alkoxyalkylmoiety. “Alkenyloxy” includes straight-chain or branched alkenyloxymoieties. Examples of “alkenyloxy” include H₂C═CHCH₂O, (CH₃)₂C═CHCH₂O,(CH₃)CH═CHCH₂O, (CH₃)CH═C(CH₃)CH₂O and CH₂═CHCH₂CH₂O. “Alkynyloxy”includes straight-chain or branched alkynyloxy moieties. Examples of“alkynyloxy” include HC≡CCH₂O, CH₃C≡CCH₂O and CH₃C≡CCH₂CH₂O. “Alkylthio”includes branched or straight-chain alkylthio moieties such asmethylthio, ethylthio, and the different propylthio, butylthio,pentylthio and hexylthio isomers. “Alkylsulfinyl” includes bothenantiomers of an alkylsulfinyl group. Examples of “alkylsulfinyl”include CH₃S(O)—, CH₃CH₂S(O)—, CH₃CH₂CH₂S(O)—, (CH₃)₂CHS(O)— and thedifferent butylsulfinyl, pentylsulfinyl and hexylsulfinyl isomers.Examples of “alkyl sulfonyl” include CH₃S(O)₂—, CH₃CH₂S(O)₂—,CH₃CH₂CH₂S(O)₂—, (CH₃)₂CHS(O)₂—, and the different butylsulfonyl,pentylsulfonyl and hexylsulfonyl isomers. “Alkylthioalkyl” denotesalkylthio substitution on alkyl. Examples of “alkylthioalkyl” includeCH₃SCH₂, CH₃SCH₂CH₂, CH₃CH₂SCH₂, CH₃CH₂CH₂CH₂SCH₂ and CH₃CH₂SCH₂CH₂.“Cyanoalkyl” denotes an alkyl group substituted with one cyano group.Examples of “cyanoalkyl” include NCCH₂, NCCH₂CH₂ and CH₃CH(CN)CH₂.“Alkylamino”, “dialkylamino”, and the like, are defined analogously tothe above examples. The terms “alkylthioalkyl”, “alkyl sulfonylamino”,“alkyl sulfonyl oxy”, “alkyl aminosulfonyl”, “alkyl sulfonyl amino”,“alkyl aminoalkyl”, “alkylsulfinylalkyl”, “alkylsulfonylalkyl”,“dialkylaminoalkyl” are defined likewise.

“Cycloalkyl” includes, for example, cyclopropyl, cyclobutyl, cyclopentyland cyclohexyl. The term “alkylcycloalkyl” denotes alkyl substitution ona cycloalkyl moiety and includes, for example, ethylcyclopropyl,i-propylcyclobutyl, 3-methylcyclopentyl and 4-methylcyclohexyl. The term“cycloalkylalkyl” denotes cycloalkyl substitution on an alkyl moiety.The term “cycloalkylalkenyl” denotes cycloalkyl substitution on analkenyl moiety. The term “cycloalkylalkynyl” denotes cycloalkylsubstitution on an alkynyl moiety. Examples of “cycloalkylalkyl” includecyclopropylmethyl, cyclopentylethyl, and other cycloalkyl moietiesbonded to straight-chain or branched alkyl groups. The term“cycloalkoxy” denotes cycloalkyl linked through an oxygen atom such ascyclopentyloxy and cyclohexyloxy. “Cycloalkylalkoxy” denotescycloalkylalkyl linked through an oxygen atom attached to the alkylchain. Examples of “cycloalkylalkoxy” include cyclopropylmethoxy,cyclopentylethoxy, and other cycloalkyl moieties bonded tostraight-chain or branched alkoxy groups. “Cycloalkenyl” includes groupssuch as cyclopentenyl and cyclohexenyl as well as groups with more thanone double bond such as 1,3- and 1,4-cyclohexadienyl. The term“cycloalkylcycloalkyl” means a cycloalkyl substitution on a cycloalkylmoiety”. The terms “cycloalkoxyalkyl”, “alkylcycloalkylalkyl”,“cycloalkylaminoalkyl”, “cycloalkylthio”, “cycloalkylsulfinyl”,“cycloalkylsulfonyl” and the like are defined likewise.

The term “halogen”, either alone or in compound words such as“haloalkyl”, or when used in descriptions such as “alkyl substitutedwith halogen” includes fluorine, chlorine, bromine or iodine. Further,when used in compound words such as “haloalkyl”, or when used indescriptions such as “alkyl substituted with halogen” said alkyl may bepartially or fully substituted with halogen atoms which may be the sameor different. Examples of “haloalkyl” or “alkyl substituted withhalogen” include F₃C, ClCH₂, CF₃CH₂ and CF₃CCl₂. The terms“halocycloalkyl”, “halocycloalkoxy”, “halocycloalkenyl”,“halocycloalkylalkyl”, “haloalkoxy”, “haloalkoxyhaloalkoxy”,“haloalkylaminoalkyl”, “haloalkylcarbonylamino” “haloalkylthio”,“haloalkylsulfonylamino”, “haloalkenyl”, “haloalkynyl”,“haloalkylcarbonyloxy”, “haloalkylsulfonyloxy”, “haloalkynyloxy”, andthe like, areis defined analogously to the term “haloalkyl”. Examples of“haloalkoxy” include CF₃O—, CCl₃CH₂O—, HCF₂CH₂CH₂O— and CF₃CH₂O—.Examples of “haloalkylthio” include CCl₃S—, CF₃S—, CCl₃CH₂S— andClCH₂CH₂CH₂S—. Examples of “haloalkylsulfinyl” include CF₃S(O)—,CCl₃S(O)—, CF₃CH₂S(O)— and CF₃CF₂S(O)—. Examples of “haloalkylsulfonyl”include CF₃S(O)₂—, CCl₃S(O)₂—, CF₃CH₂S(O)₂— and CF₃CF₂S(O)₂—. Examplesof “haloalkenyl” include (Cl)₂C═CHCH₂— and CF₃CH₂CH═CHCH₂—. Examples of“haloalkynyl” include HC═CCHCl—, CF₃C≡C—, CCl₃C≡C— and FCH₂C≡CCH₂—.Examples of “haloalkoxyalkoxy” include CF₃OCH₂O—, ClCH₂CH₂OCH₂CH₂O—,Cl₃CCH₂OCH₂O— as well as branched alkyl derivatives. Examples of the“haloalkenyloxy” include (Cl)₂C═CHCH₂O— and CF₃CH₂CH═CHCH₂O—. Examplesof “haloalkoxyalkyl” include CF₃OCH₂—, CCl₃CH₂OCH₂—, HCF₂CH₂CH₂OCH₂— andCF₃CH₂OCH₂—.

“Alkylcarbonyl” denotes a straight-chain or branched alkyl moietiesbonded to a C(═O) moiety. Examples of “alkylcarbonyl” include CH₃C(═O)—,CH₃CH₂CH₂C(═O)— and (CH₃)₂CHC(═O)—. Examples of “alkoxycarbonyl” includeCH₃OC(═O)—, CH₃CH₂OC(═O)—, CH₃CH₂CH₂OC(═O)—, (CH₃)₂CHOC(═O)— and thedifferent butoxy- or pentoxycarbonyl isomers. The terms“alkylcarbonylalkyl”, “alkylcarbonyloxy”, “alkylcarbonylalkoxy”,“alkylcarbonylamino”, “alkoxycarbonylamino”, “alkylaminocarbonyl”,“dialkylaminosulfonyl” “cycloalkylcarbonyl”, “cycloalkylalkoxycarbonyl”,“cycloalkoxycarbonyl”, “cycloalkylcarbonyloxy”, “dialkylaminocarbonyl”“cycloalkylaminocarbonyl”, “haloalkylcarbonyl” and “haloalkoxycarbonyl”are defined likewise. The term “hydroxyalkyl” refers to a hydroxy groupattached to an alkyl group. The term “cyanoalkyl” refers to a cyanogroup attached to an alkyl group. The term “cyanoalkoxy” refers to acyano group attached to an alkoxy group. The term “nitroalkyl” refers toa nitro group attached to an alkyl group. The term “nitroalkenyl” refersto a nitro group attached to an alkenyl group.

The term “trialkylsilyl” means silyl substituted with three alkylgroups. The term “trialkylsilylalkyl” means refers to a trialkylsilylgroup bonded through an alkyl group (e.g. —CH₂TMS). The term“trialkylsilyloxy” means refers to a trialkylsilyl group bonded throughoxygen (e.g. —OTMS).

The total number of carbon atoms in a substituent group is indicated bythe “C_(j)-C_(j)” prefix where i and j are numbers from 1 to 12. Forexample, C₁-C₄ alkylsulfonyl designates methylsulfonyl throughbutylsulfonyl; C₂ alkoxyalkyl designates CH₃OCH₂—; C₃ alkoxyalkyldesignates, for example, CH₃CH(OCH₃)—, CH₃OCH₂CH₂— or CH₃CH₂OCH₂—; andC₄ alkoxyalkyl designates the various isomers of an alkyl groupsubstituted with an alkoxy group containing a total of four carbonatoms, examples including CH₃CH₂CH₂OCH₂— and CH₃CH₂OCH₂CH₂—.

When a compound is substituted with a substituent bearing a subscriptthat indicates the number of said substituents can exceed 1, saidsubstituents (when they exceed 1) are independently selected from thegroup of defined substituents, e.g., S(═O)_(u)(═NR⁸)_(v), u and v areindependently 0, 1 or 2). When a group contains a substituent which canbe hydrogen, for example (R⁵ or R⁶), then when this substituent is takenas hydrogen, it is recognized that this is equivalent to said groupbeing unsubstituted. When a variable group is shown to be optionallyattached to a position, for example R⁹ and R¹¹ wherein n may be 0, thenhydrogen may be at the position even if not recited in the variablegroup definition. When one or more positions on a group are said to be“not substituted” or “unsubstituted”, then hydrogen atoms are attachedto take up any free valency.

Unless otherwise indicated, a “ring” or “ring system” as a component ofFormula 1 (e.g., substituent Q¹ and Q² is heterocyclic). The term “ringsystem” denotes two or more fused rings. The terms “bicyclic ringsystem” and “fused bicyclic ring system” denote a ring system consistingof two fused rings, in which either ring can be saturated, partiallyunsaturated, or fully unsaturated unless otherwise indicated. The term“fused heterobicyclic ring system” denotes a fused bicyclic ring systemin which at least one ring atom is not carbon. The term “ring member”refers to an atom or other moiety (e.g., C(═O), C(═S), S(O) or S(O)₂)forming the backbone of a ring or ring system.

The terms “heterocyclic ring”, “heterocycle” or “heterocyclic ringsystem” denote a ring or ring system in which at least one atom formingthe ring backbone is not carbon, e.g., nitrogen, oxygen or sulfur.Typically a heterocyclic ring contains no more than 4 nitrogens, no morethan 2 oxygens and no more than 2 sulfurs. Unless otherwise indicated, aheterocyclic ring can be a saturated, partially unsaturated, or fullyunsaturated ring. When a fully unsaturated heterocyclic ring satisfiesHückel's rule, then said ring is also called a “heteroaromatic ring” or“aromatic heterocyclic ring”. Unless otherwise indicated, heterocyclicrings and ring systems can be attached through any available carbon ornitrogen by replacement of a hydrogen on said carbon or nitrogen.

“Aromatic” indicates that each of the ring atoms is essentially in thesame plane and has a p-orbital perpendicular to the ring plane, and that(4n+2) π electrons, where n is a positive integer, are associated withthe ring to comply with Hückel's rule. The term “aromatic ring system”denotes a carbocyclic or heterocyclic ring system in which at least onering of the ring system is aromatic. The term “aromatic heterocyclicring system” denotes a heterocyclic ring system in which at least onering of the ring system is aromatic. The term “nonaromatic ring system”denotes a carbocyclic or heterocyclic ring system that may be fullysaturated, as well as partially or fully unsaturated, provided that noneof the rings in the ring system are aromatic.

The term “optionally substituted” in connection with the heterocyclicrings refers to groups which are unsubstituted or have at least onenon-hydrogen substituent that does not extinguish the biologicalactivity possessed by the unsubstituted analog. As used herein, thefollowing definitions shall apply unless otherwise indicated. The term“optionally substituted” is used interchangeably with the phrase“substituted or unsubstituted” or with the term “(un)substituted.”Unless otherwise indicated, an optionally substituted group may have asubstituent at each substitutable position of the group, and eachsubstitution is independent of the other.

As noted above, Q¹ can be (among others) phenyl optionally substitutedwith one or more substituents selected from a group of substituents asdefined in the Summary of the Invention. An example of phenyl optionallysubstituted with one to five substituents is the ring illustrated as U-1in Exhibit 1, wherein R^(v) is R⁹ as defined in the Summary of theInvention for Q¹ and R^(v) is R¹¹ as defined in the Summary of theInvention for Q² and r is an integer from 0 to 5.

As noted above, Q¹ can be (among others) 5- or 6-membered fullyunsaturated heterocyclic ring, which may be saturated or unsaturated,optionally substituted with one or more substituents selected from agroup of substituents as defined in the Summary of the Invention.Examples of a 5- or 6-membered unsaturated aromatic heterocyclic ringoptionally substituted with from one or more substituents include therings U-2 through U-61 illustrated in Exhibit 1 wherein R^(v) is anysubstituent as defined in the Summary of the Invention for Q¹ (i.e. R⁹)and r is an integer from 0 to 5, limited by the number of availablepositions on each U group. As U-29, U-30, U-36, U-37, U-38, U-39, U-40,U-41, U-42 and U-43 have only one available position, for these U groupsr is limited to the integers 0 or 1, and r being 0 means that the Ugroup is unsubstituted and a hydrogen is present at the positionindicated by (R^(v))_(r).

Examples of a 5- or 6-membered saturated or non-aromatic unsaturatedheterocyclic ring containing ring members selected from up to two Oatoms and up to two S atoms and up to 4 N atoms, and optionallysubstituted on carbon atom ring members with up to five halogen atomsincludes the rings G-1 through G-35 as illustrated in Exhibit 2. Notethat when the attachment point on the G group is illustrated asfloating, the G group can be attached to the remainder of Formula 1through any available carbon or nitrogen of the G group by replacementof a hydrogen atom. The optional substituents corresponding to R^(v) canbe attached to any available carbon or nitrogen by replacing a hydrogenatom. For these G rings, r is typically an integer from 0 to 5, limitedby the number of available positions on each G group.

Note that when Q¹ or Q² comprises a ring selected from G-28 throughG-35, G² is selected from O, S or N. Note that when G² is N, thenitrogen atom can complete its valence by substitution with either H orthe substituents corresponding to R^(v) as defined in the Summary of theInvention for Q¹ or Q².

As noted above, Q¹ can be (among others) an 8-, 9- or 10-memberedheteroaromatic bicyclic ring system optionally substituted with one ormore substituents selected from a group of substituents as defined inthe Summary of the Invention (i.e. R⁹ and R¹¹). Examples of 8-, 9- or10-membered heteraromatic bicyclic ring system optionally substitutedwith from one or more substituents include the rings U-81 through U-123illustrated in Exhibit 3 wherein R^(v) is any substituent as defined inthe Summary of the Invention for Q¹ (i.e. R⁸), and r is typically aninteger from 0 to 5.

Although R^(v) groups are shown in the structures U-1 through U-123, itis noted that they do not need to be present since they are optionalsubstituents. Note that when R^(v) is H when attached to an atom, thisis the same as if said atom is unsubstituted. The nitrogen atoms thatrequire substitution to fill their valence are substituted with H orR^(v). Note that when the attachment point between (R^(v))_(r) and the Ugroup is illustrated as floating, (R^(v))_(r) can be attached to anyavailable carbon atom or nitrogen atom of the U group. Note that whenthe attachment point on the U group is illustrated as floating, the Ugroup can be attached to the remainder of Formula 1 through anyavailable carbon or nitrogen of the U group by replacement of a hydrogenatom. Note that some U groups can only be substituted with less than 4R^(v) groups (e.g., U-2 through U-5, U-7 through U-48, and U-52 throughU-61).

A wide variety of synthetic methods are known in the art to enablepreparation of aromatic and nonaromatic heterocyclic rings and ringsystems; for extensive reviews see the eight volume set of ComprehensiveHeterocyclic Chemistry, A. R. Katritzky and C. W. Rees editors-in-chief,Pergamon Press, Oxford, 1984 and the twelve volume set of ComprehensiveHeterocyclic Chemistry II, A. R. Katritzky, C. W. Rees and E. F. V.Scriven editors-in-chief, Pergamon Press, Oxford, 1996.

Compounds of this invention can exist as one or more stereoisomers. Thevarious stereoisomers include enantiomers, diastereomers, atropisomersand geometric isomers. Stereoisomers are isomers of identicalconstitution but differing in the arrangement of their atoms in spaceand include enantiomers, diastereomers, cis-trans isomers (also known asgeometric isomers) and atropisomers. Atropisomers result from restrictedrotation about single bonds where the rotational barrier is high enoughto permit isolation of the isomeric species. One skilled in the art willappreciate that one stereoisomer may be more active and/or may exhibitbeneficial effects when enriched relative to the other stereoisomer(s)or when separated from the other stereoisomer(s). Additionally, theskilled artisan knows how to separate, enrich, and/or to selectivelyprepare said stereoisomers. The compounds of the invention may bepresent as a mixture of stereoisomers, individual stereoisomers or as anoptically active form.

When enantiomerically enriched, one enantiomer is present in greateramounts than the other, and the extent of enrichment can be defined byan expression of enantiomeric excess (“ee”), which is defined as(2x-1)·100%, where x is the mole fraction of the dominant enantiomer inthe mixture (e.g., an ee of 20% corresponds to a 60:40 ratio ofenantiomers).

Preferably the compositions of this invention have at least a 50%enantiomeric excess; more preferably at least a 75% enantiomeric excess;still more preferably at least a 90% enantiomeric excess; and the mostpreferably at least a 94% enantiomeric excess of the more active isomer.Of particular note are enantiomerically pure embodiments of the moreactive isomer.

Compounds of Formula 1 can comprise additional chiral centers. Forexample, substituents and other molecular constituents such as R² and R³may themselves contain chiral centers. This invention comprises racemicmixtures as well as enriched and essentially pure stereoconfigurationsat these additional chiral centers.

Compounds of this invention can exist as one or more conformationalisomers due to restricted rotation about the amide bond (e.g.,C(Y)N(Q²)(R⁷)) in Formula 1. This invention comprises mixtures ofconformational isomers. In addition, this invention includes compoundsthat are enriched in one conformer relative to others.

Compounds of Formula 1 typically exist in more than one form, andFormula 1 thus include all crystalline and non-crystalline forms of thecompounds they represent. Non-crystalline forms include embodimentswhich are solids such as waxes and gums as well as embodiments which areliquids such as solutions and melts. Crystalline forms includeembodiments which represent essentially a single crystal type andembodiments which represent a mixture of polymorphs (i.e. differentcrystalline types). The term “polymorph” refers to a particularcrystalline form of a chemical compound that can crystallize indifferent crystalline forms, these forms having different arrangementsand/or conformations of the molecules in the crystal lattice. Althoughpolymorphs can have the same chemical composition, they can also differin composition due the presence or absence of co-crystallized water orother molecules, which can be weakly or strongly bound in the lattice.Polymorphs can differ in such chemical, physical and biologicalproperties as crystal shape, density, hardness, color, chemicalstability, melting point, hygroscopicity, suspensibility, dissolutionrate and biological availability. One skilled in the art will appreciatethat a polymorph of a compound of Formula 1 can exhibit beneficialeffects (e.g., suitability for preparation of useful formulations,improved biological performance) relative to another polymorph or amixture of polymorphs of the same compound of Formula 1. Preparation andisolation of a particular polymorph of a compound of Formula 1 can beachieved by methods known to those skilled in the art including, forexample, crystallization using selected solvents and temperatures. For acomprehensive discussion of polymorphism see R. Hilfiker, Ed.,Polymorphism in the Pharmaceutical Industry, Wiley-VCH, Weinheim, 2006.

One skilled in the art will appreciate that not all nitrogen-containingheterocycles can form N-oxides since the nitrogen requires an availablelone pair for oxidation to the oxide; one skilled in the art willrecognize those nitrogen-containing heterocycles which can formN-oxides. One skilled in the art will also recognize that tertiaryamines can form N-oxides. Synthetic methods for the preparation ofN-oxides of heterocycles and tertiary amines are very well known by oneskilled in the art including the oxidation of heterocycles and tertiaryamines with peroxy acids such as peracetic and m-chloroperbenzoic acid(MCPBA), hydrogen peroxide, alkyl hydroperoxides such as t-butylhydroperoxide, sodium perborate, and dioxiranes such asdimethyldioxirane. These methods for the preparation of N-oxides havebeen extensively described and reviewed in the literature, see forexample: T. L. Gilchrist in Comprehensive Organic Synthesis, vol. 7, pp748-750, S. V. Ley, Ed., Pergamon Press; M. Tisler and B. Stanovnik inComprehensive Heterocyclic Chemistry, vol. 3, pp 18-20, A. J. Boultonand A. McKillop, Eds., Pergamon Press; M. R. Grimmett and B. R. T. Keenein Advances in Heterocyclic Chemistry, vol. 43, pp 149-161, A. R.Katritzky, Ed., Academic Press; M. Tisler and B. Stanovnik in Advancesin Heterocyclic Chemistry, vol. 9, pp 285-291, A. R. Katritzky and A. J.Boulton, Eds., Academic Press; and G. W. H. Cheeseman and E. S. G.Werstiuk in Advances in Heterocyclic Chemistry, vol. 22, pp 390-392, A.R. Katritzky and A. J. Boulton, Eds., Academic Press.

One skilled in the art recognizes that because in the environment andunder physiological conditions salts of chemical compounds are inequilibrium with their corresponding nonsalt forms, salts share thebiological utility of the nonsalt forms. Thus a wide variety of salts ofa compound of Formula 1 are useful for control of undesired vegetation(i.e. are agriculturally suitable). The salts of a compound of Formula 1include acid-addition salts with inorganic or organic acids such ashydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic,butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic,tartaric, 4-toluenesulfonic or valeric acids. When a compound of Formula1 contains an acidic moiety such as a carboxylic acid or phenol, saltsalso include those formed with organic or inorganic bases such aspyridine, triethylamine or ammonia, or amides, hydrides, hydroxides orcarbonates of sodium, potassium, lithium, calcium, magnesium or barium.Accordingly, the present invention comprises compounds selected fromFormula 1, N-oxides and agriculturally suitable salts thereof.

Embodiments of the present invention as described in the Summary of theInvention include (where Formula 1 as used in the following Embodimentsincludes N-oxides and salts thereof) the following:

Embodiment 1

A compound of Formula 1 (including all stereoisomers), N-oxides, andsalts thereof, agricultural compositions containing them and their useas herbicides as described in the Summary of the Invention.

Embodiment 2

A compound of Embodiment 1 wherein is a phenyl or benzyl ring or anaphthalenyl ring system, each ring or ring system optionallysubstituted with up to 5 substituents independently selected from R⁹; ora 5- to 6-membered fully unsaturated heterocyclic ring, each ring orring system containing ring members selected from carbon atoms and 1 to4 heteroatoms independently selected from up to 2 O, up to 2 S and up to4 N atoms, wherein up to 3 carbon ring members are independentlyselected from C(═O) and C(═S), and the sulfur atom ring members areindependently selected from S(═O)_(u)(═NR⁸)_(v), each ring or ringsystem optionally substituted with up to 5 substituents independentlyselected from R⁹ on carbon atom ring members and selected from R¹⁰ onnitrogen atom ring members.

Embodiment 3

A compound of Embodiment 2 wherein Q¹ is a phenyl ring optionallysubstituted with up to 5 substituents independently selected from R⁹; ora 5- to 6-membered fully unsaturated heterocyclic ring, each ringcontaining ring members selected from carbon atoms and 1 to 4heteroatoms independently selected from up to 2 O, up to 2 S and up to 4N atoms, wherein up to 3 carbon ring members are independently selectedfrom C(═O) and C(═S), and the sulfur atom ring members are independentlyselected from S(═O)_(u)(═NR⁸)_(v), each ring or ring system optionallysubstituted with up to 5 substituents independently selected from R⁹ oncarbon atom ring members and selected from R¹⁰ on nitrogen atom ringmembers.

Embodiment 4

A compound of Embodiment 3 wherein Q¹ is a phenyl ring optionallysubstituted with up to 5 substituents independently selected from R⁹.

Embodiment 5

A compound of Embodiment 4 wherein Q¹ is a phenyl ring substituted with1 to 3 substituents independently selected from R⁹.

Embodiment 6

A compound of Embodiment 5 wherein Q¹ is a phenyl ring substituted with1 to 2 substituents independently selected from R⁹.

Embodiment 7

A compound of Embodiment 6 wherein Q¹ is a phenyl ring having asubstituent selected from R⁹ at the para (4-) position (and optionallyother substituents).

Embodiment 8

A compound of Embodiment 7 wherein when Q¹ is a phenyl ring substitutedwith at least two substituents selected from R⁹, then one substituent isat the para (4-) position and at least one other substituent is at ameta position (of the phenyl ring).

Embodiment 9

A compound of any one of Embodiments 1 through 3 wherein Q¹ is a 5- to6-membered fully unsaturated heterocyclic ring, each ring containingring members selected from carbon atoms and 1 to 3 heteroatomsindependently selected from up to 1 O, up to 1 S and up to 2 N atoms,wherein up to 2 carbon ring members are independently selected fromC(═O) and C(═S), and the sulfur atom ring members are independentlyselected from S(═O)_(u)(═NR⁸)_(v), each ring optionally substituted withup to 5 substituents independently selected from R⁹ on carbon atom ringmembers and selected from R¹⁰ on nitrogen atom ring members.

Embodiment 10

A compound of Embodiment 9 wherein Q² is a phenyl ring or a naphthalenylring system, each ring or ring system optionally substituted with up to5 substituents independently selected from R¹¹; or a 5- to 6-memberedfully unsaturated heterocyclic ring, each ring containing ring membersselected from carbon atoms and 1 to 4 heteroatoms independently selectedfrom up to 1 O, up to 1 S and up to 2 N atoms, wherein up to 2 carbonring members are independently selected from C(═O) and C(═S), and thesulfur atom ring members are independently selected fromS(═O)_(u)(═NR⁸)_(v), each ring or ring system optionally substitutedwith up to 5 substituents independently selected from R¹¹ on carbon atomring members and selected from R¹² on nitrogen atom ring members.

Embodiment 11

A compound of Embodiment 10 wherein Q² is a phenyl ring optionallysubstituted with up to 5 substituents independently selected from R¹¹.

Embodiment 12

A compound of Embodiment 11 wherein Q² is a phenyl ring optionallysubstituted with up to 3 substituents independently selected from R¹¹.

Embodiment 13

A compound of Embodiment 12 wherein Q² is a phenyl ring substituted with1 substituent independently selected from R¹¹ at the 3-position.

Embodiment 14

A compound of Embodiment 10 wherein Q² is 5- to 6-membered fullyunsaturated heterocyclic ring, each ring containing ring membersselected from carbon atoms and 1 to 4 heteroatoms independently selectedfrom up to 1 O, up to 1 S and up to 2 N atoms, wherein up to 2 carbonring members are independently selected from C(═O) and C(═S), and thesulfur atom ring members are independently selected fromS(═O)_(u)(═NR⁸)_(v), each ring or ring system optionally substitutedwith up to 5 substituents independently selected from R¹¹ on carbon atomring members and selected from R¹² on nitrogen atom ring members.

Embodiment 15

A compound of any one of Embodiments 1 through 14 wherein R¹ and R² areeach independently H, halogen or C₁-C₄ alkyl.

Embodiment 16

A compound of Embodiment 15 wherein R¹ and R² are each independently H,Cl, or CH₃.

Embodiment 17

A compound of Embodiment 16 wherein R¹ and R² are each independently Hor Cl.

Embodiment 18

A compound of Embodiment 17 wherein R¹ and R² are each H.

Embodiment 19

A compound any one of Embodiments 1 through 16 wherein Y is O or S.

Embodiment 20

A compound of Embodiment 19 wherein Y is O.

Embodiment 21

A compound of Embodiment 19 wherein Y is S.

Embodiment 22

A compound of any one of Embodiments 1 through 21 wherein A is asaturated, partially unsaturated or fully unsaturated chain containing 2to 4 atoms selected from up to 3 carbon, up to 1 O, up to 1 S and up to1 N atoms, wherein up to 2 carbon members are independently selectedfrom C(═O) and C(═S) and the sulfur atom member is selected fromS(═O)_(u)(═NR⁸)_(v); the said chain optionally substituted with up to 3substituents independently selected from R³ on carbon atoms and R⁴ onnitrogen atoms.

Embodiment 23

A compound of Embodiment 22 wherein A is a saturated or partiallyunsaturated chain containing 2 to 4 atoms selected from up to 2 carbonand up to 1 N atoms, wherein up to 1 carbon member is independentlyselected from C(═O) and C(═S); the said chain optionally substitutedwith up to 2 substituents independently selected from R³ on carbon atomsand R⁴ on nitrogen atoms.

Embodiment 24

A compound of Embodiment 23 wherein A is a saturated or partiallyunsaturated chain containing 2 to 3 atoms selected from up to 2 carbonand up to 1 N atoms, wherein up to 1 carbon member is independentlyselected from C(═O); the said chain optionally substituted with up to 1substituent independently selected from R³ on carbon atoms and R⁴ onnitrogen atoms.

Embodiment 25

A compound of Embodiment 24 wherein A is —CH₂CH₂CH₂—, —NCH₂—, —C(═O)CH₂—or —CH═CH— wherein the bond projecting to the left is connected tonitrogen of the —N-J- moiety, and the bond projecting to the right isconnected to the nitrogen of the —N═C— (or —N—CH—) moiety of Formula 1.

Embodiment 26

A compound of Embodiment 25 wherein A is —CH₂CH₂CH₂—.

Embodiment 27

A compound of Embodiment 25 wherein A is —NCH₂— wherein the bondprojecting to the left is connected to nitrogen of the —N-J- moiety, andthe bond projecting to the right is connected to the nitrogen of the—N═C— moiety of Formula 1.

Embodiment 28

A compound of Embodiment 25 wherein A is —C(═O)CH₂— wherein the bondprojecting to the left is connected to nitrogen of the —N-J- moiety, andthe bond projecting to the right is connected to the nitrogen of the—N═C— moiety of Formula 1.

Embodiment 29

A compound of Embodiment 25 wherein A is —CH═CH—.

Embodiment 30

A compound of any one of Embodiments 1 through 29 wherein each R³ isindependently halogen, cyano, hydroxy, —CO₂H, C₁-C₄ alkyl, C₁-C₄haloalkyl, C₁-C₄ alkoxy, C₁-C₄ alkylthio, C₃-C₆ cycloalkyl or C₄-C₆cycloalkylalkyl.

Embodiment 31

A compound of Embodiment 30 wherein each R³ is independently cyano,—CO₂H, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₄ alkylthio or C₄-C₆cycloalkylalkyl.

Embodiment 32

A compound of Embodiment 31 wherein each R³ is independently cyano,—CO₂H, C₁-C₄ alkyl or C₁-C₄ haloalkyl.

Embodiment 33

A compound of Embodiment 32 wherein each R³ is independently cyano,—CO₂H or C₁-C₄ alkyl.

Embodiment 34

A compound of Embodiment 1 wherein two R³ are taken together with thecarbon atom(s) to which they are bonded to form a C₄ cycloalkyl ring.

Embodiment 35

A compound of any one of Embodiments 1 through 34 wherein each R⁴ isindependently C₁-C₄ alkyl, C₁-C₄ haloalkyl or C₃-C₆ cycloalkyl.

Embodiment 36

A compound of Embodiment 35 wherein each R⁴ is independently C₁-C₄alkyl.

Embodiment 37

A compound of Embodiment 36 wherein each R⁴ is CH₃.

Embodiment 38

A compound of any one of Embodiments 1 through 37 wherein J is —CR⁵R⁶—.

Embodiment 39

A compound of any one of Embodiments 1 through 37 wherein J is—CR⁵R⁶—CR^(5a)R^(6a)— wherein the —CR⁵R⁶— moiety is directly connectedto N.

Embodiment 40

A compound of Embodiment 38 wherein J is —CH₂—.

Embodiment 41

A compound of Embodiment 39 wherein J is —CH₂CH₂—.

Embodiment 42

A compound of any one of Embodiments 1 through 39 wherein R⁵ and R⁶ areeach independently H, halogen, hydroxy or CH₃.

Embodiment 43

A compound of Embodiment 42 wherein R⁵ and R⁶ are each independently Hor halogen.

Embodiment 44

A compound of Embodiment 43 wherein R⁵ and R⁶ are each H.

Embodiment 45

A compound of any one of Embodiments 1 through 39 wherein R⁵ and R⁶ aretaken together with the carbon atom to which they are bonded to form aC₄ cycloalkyl ring.

Embodiment 46

A compound of any one of Embodiment 1 through 39 wherein Rya and R^(6a)are each independently H or C₁-C₄ alkyl.

Embodiment 47

A compound of any one of Embodiments 1 through 46 wherein R⁷ is H,hydroxy, amino, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₃-C₆alkynyl, C₂-C₈ alkoxyalkyl, C₂-C₈ haloalkoxyalkyl, C₂-C₈ alkylthioalkyl,C₂-C₈ alkylsulfinylalkyl, C₂-C₈ alkylsulfonylalkyl, C₂-C₈ alkylcarbonyl,C₂-C₈ haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, C₂-C₈alkoxycarbonyl, C₂-C₈ haloalkoxycarbonyl, C₄-C₁₀ cycloalkoxycarbonyl,C₂-C₈ alkylaminocarbonyl, C₃-C₁₀ dialkylaminocarbonyl or C₄-C₁₀cycloalkylaminocarbonyl.

Embodiment 48

A compound of Embodiment 47 wherein R⁷ is H, hydroxy, amino, C₁-C₆alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₃-C₆ alkynyl, C₂-C₈ alkoxyalkyl,C₂-C₈ haloalkoxyalkyl or C₂-C₈ alkylthioalkyl.

Embodiment 49

A compound of Embodiment 48 wherein R⁷ is H, C₁-C₆ alkyl, C₂-C₆ alkenyl,C₃-C₆ alkynyl or C₂-C₈ alkoxyalkyl.

Embodiment 50

A compound of Embodiment 49 wherein R⁷ is H or C₁-C₆ alkyl.

Embodiment 51

A compound of any one of Embodiments 1 through 50 wherein each R⁸ isindependently H, cyano or C₂-C₃ alkylcarbonyl.

Embodiment 52

A compound of Embodiment 51 wherein each R⁸ is independently H.

Embodiment 53

A compound of any one of Embodiments 1 through 52 wherein each R⁹ isindependently halogen, cyano, nitro, C₁-C₈ alkyl, C₁-C₄ cyanoalkyl,C₁-C₄ cyanoalkoxy, C₁-C₈ haloalkyl, C₁-C₈ nitroalkyl, C₂-C₈ alkenyl,C₂-C₈ haloalkenyl, C₂-C₈ nitroalkenyl, C₂-C₈ alkynyl, C₂-C₈ haloalkynyl,C₄-C₁₀ cycloalkylalkyl, C₄-C₁₀ halocycloalkylalkyl, C₅-C₁₂alkylcycloalkylalkyl, C₅-C₁₂ cycloalkylalkenyl, C₅-C₁₂cycloalkylalkynyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₄-C₁₀alkylcycloalkyl, C₆-C₁₂ cycloalkylcycloalkyl, C₃-C₈ cycloalkenyl, C₃-C₈halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₂-C₈ haloalkoxyalkyl, C₃-C₈haloalkoxyalkoxy, C₁-C₄ hydroxyalkyl, C₄-C₁₀ cycloalkoxyalkyl, C₃-C₁₀alkoxyalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈alkylsulfonylalkyl, C₂-C₈ alkylaminoalkyl, C₂-C₈ haloalkylaminoalkyl,C₄-C₁₀ cycloalkylaminoalkyl, C₃-C₁₀ dialkylaminoalkyl, —CHO, C₂-C₈alkylcarbonyl, C₂-C₈ haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl,—C(═O)OH, C₂-C₈ alkoxycarbonyl, C₂-C₈ haloalkoxycarbonyl, C₄-C₁₀cycloalkoxycarbonyl, C₅-C₁₂ cycloalkylalkoxycarbonyl, —C(═O)NH₂, C₂-C₈alkylaminocarbonyl, C₄-C₁₀ cycloalkylaminocarbonyl, C₃-C₁₀dialkylaminocarbonyl, C₁-C₈ alkoxy, C₁-C₈ haloalkoxy, C₂-C₈alkoxyalkoxy, C₂-C₈ alkenyloxy, C₂-C₈ haloalkenyloxy, C₂-C₈haloalkoxyhaloalkoxy, C₃-C₈ alkynyloxy, C₃-C₈ haloalkynyloxy, C₃-C₈cycloalkoxy, C₃-C₈ halocycloalkoxy, C₄-C₁₀ cycloalkylalkoxy, C₃-C₁₀alkylcarbonylalkoxy, C₂-C₈ alkylcarbonyloxy, C₂-C₈ haloalkylcarbonyloxyor C₄-C₁₀ cycloalkylcarbonyloxy.

Embodiment 54

A compound of Embodiment 53 wherein each R⁹ is independently halogen,cyano, nitro, C₁-C₈ alkyl, C₁-C₄ cyanoalkyl, C₁-C₄ cyanoalkoxy, C₁-C₈haloalkyl, C₁-C₈ nitroalkyl, C₂-C₈ alkenyl, C₂-C₈ haloalkenyl, C₂-C₈nitroalkenyl, C₂-C₈ alkynyl, C₂-C₈ haloalkynyl, C₄-C₁₀ cycloalkylalkyl,C₄-C₁₀ halocycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₅-C₁₂cycloalkylalkenyl, C₅-C₁₂ cycloalkylalkynyl, C₃-C₈ cycloalkyl, C₃-C₈halocycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₆-C₁₂ cycloalkylcycloalkyl,C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₂-C₈haloalkoxyalkyl, C₃-C₈ haloalkoxyalkoxy, C₁-C₄ hydroxyalkyl, C₄-C₁₀cycloalkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈alkylsulfinylalkyl, C₂-C₈ alkylsulfonylalkyl, C₂-C₈ alkylaminoalkyl,C₂-C₈ haloalkylaminoalkyl, C₄-C₁₀ cycloalkylaminoalkyl or C₃-C₁₀dialkylaminoalkyl.

Embodiment 55

A compound of Embodiment 54 wherein each R⁹ is independently halogen,cyano, nitro, C₁-C₈ alkyl, C₁-C₄ cyanoalkyl, C₁-C₄ cyanoalkoxy, C₁-C₈haloalkyl, C₁-C₈ nitroalkyl, C₂-C₈ alkenyl, C₂-C₈ haloalkenyl, C₂-C₈nitroalkenyl, C₂-C₈ alkynyl, C₂-C₈ haloalkynyl, C₄-C₁₀ cycloalkylalkyl,C₄-C₁₀ halocycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₅-C₁₂cycloalkylalkenyl, C₅-C₁₂ cycloalkylalkynyl, C₃-C₈ cycloalkyl, C₃-C₈halocycloalkyl, C₄-C₁₀ alkylcycloalkyl or C₆-C₁₂ cycloalkylcycloalkyl.

Embodiment 56

A compound of Embodiment 55 wherein each R⁹ is independently halogen,cyano, nitro, C₁-C₈ alkyl, C₁-C₄ cyanoalkyl, C₁-C₄ cyanoalkoxy or C₁-C₈haloalkyl.

Embodiment 57

A compound of Embodiment 56 wherein each R⁹ is independently halogen orC₁-C₈ haloalkyl.

Embodiment 58

A compound of Embodiment 57 wherein each R⁹ is independently F, Cl orCF₃.

Embodiment 59

A compound of Embodiment 58 wherein each R⁹ is independently F or CF₃.

Embodiment 60

A compound of any one of Embodiments 1 through 59 wherein each R¹¹ isindependently halogen, cyano, nitro, C₁-C₈ alkyl, C₁-C₄ cyanoalkyl,C₁-C₄ cyanoalkoxy, C₁-C₈ haloalkyl, C₁-C₈ nitroalkyl, C₂-C₈ alkenyl,C₂-C₈ haloalkenyl, C₂-C₈ nitroalkenyl, C₂-C₈ alkynyl, C₂-C₈ haloalkynyl,C₄-C₁₀ cycloalkylalkyl, C₄-C₁₀ halocycloalkylalkyl, C₅-C₁₂alkylcycloalkylalkyl, C₅-C₁₂ cycloalkylalkenyl, C₅-C₁₂cycloalkylalkynyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₄-C₁₀alkylcycloalkyl, C₆-C₁₂ cycloalkylcycloalkyl, C₃-C₈ cycloalkenyl, C₃-C₈halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₂-C₈ haloalkoxyalkyl, C₃-C₈haloalkoxyalkoxy, C₁-C₄ hydroxyalkyl, C₄-C₁₀ cycloalkoxyalkyl, C₃-C₁₀alkoxyalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈alkylsulfonylalkyl, C₂-C₈ alkylaminoalkyl, C₂-C₈ haloalkylaminoalkyl,C₄-C₁₀ cycloalkylaminoalkyl, C₃-C₁₀ dialkylaminoalkyl, —CHO, C₂-C₈alkylcarbonyl, C₂-C₈ haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl,—C(═O)OH, C₂-C₈ alkoxycarbonyl, C₂-C₈ haloalkoxycarbonyl, C₄-C₁₀cycloalkoxycarbonyl, C₅-C₁₂ cycloalkylalkoxycarbonyl, —C(═O)NH₂, C₂-C₈alkylaminocarbonyl, C₄-C₁₀ cycloalkylaminocarbonyl, C₃-C₁₀dialkylaminocarbonyl, C₁-C₈ alkoxy, C₁-C₈ haloalkoxy, C₂-C₈alkoxyalkoxy, C₂-C₈ alkenyloxy, C₂-C₈ haloalkenyloxy, C₂-C₈haloalkoxyhaloalkoxy, C₃-C₈ alkynyloxy, C₃-C₈ haloalkynyloxy, C₃-C₈cycloalkoxy, C₃-C₈ halocycloalkoxy, C₄-C₁₀ cycloalkylalkoxy, C₃-C₁₀alkylcarbonylalkoxy, C₂-C₈ alkylcarbonyloxy, C₂-C₈ haloalkylcarbonyloxy,C₄-C₁₀ cycloalkylcarbonyloxy, C₁-C₈ alkylsulfonyloxy, C₁-C₈haloalkylsulfonyloxy, C₁-C₈ alkylthio, C₁-C₈ haloalkylthio, C₃-C₈cycloalkylthio, C₁-C₈ alkylsulfinyl, C₁-C₈ haloalkylsulfinyl, C₁-C₈alkyl sulfonyl, C₁-C₈ haloalkylsulfonyl, C₃-C₈ cycloalkylsulfonyl,formylamino, C₂-C₈ alkylcarbonylamino, C₂-C₈ haloalkylcarbonylamino orC₂-C₈ alkoxycarbonylamino.

Embodiment 61

A compound of Embodiment 60 wherein each R¹¹ is independently halogen,cyano, nitro, C₁-C₈ alkyl, C₁-C₄ cyanoalkyl, C₁-C₄ cyanoalkoxy, C₁-C₈haloalkyl, C₁-C₈ nitroalkyl, C₂-C₈ alkenyl, C₂-C₈ haloalkenyl, C₂-C₈nitroalkenyl, C₂-C₈ alkynyl, C₂-C₈ haloalkynyl, C₄-C₁₀ cycloalkylalkyl,C₄-C₁₀ halocycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₅-C₁₂cycloalkylalkenyl, C₅-C₁₂ cycloalkylalkynyl, C₃-C₈ cycloalkyl, C₃-C₈halocycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₆-C₁₂ cycloalkylcycloalkyl,C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₂-C₈haloalkoxyalkyl, C₃-C₈ haloalkoxyalkoxy, C₁-C₄ hydroxyalkyl, C₄-C₁₀cycloalkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈alkylsulfinylalkyl, C₂-C₈ alkylsulfonylalkyl, C₁-C₈ alkylsulfonyloxy,C₁-C₈ haloalkylsulfonyloxy, C₁-C₈ alkylthio, C₁-C₈ haloalkylthio, C₃-C₈cycloalkylthio, C₁-C₈ alkylsulfinyl, C₁-C₈ haloalkylsulfinyl, C₁-C₈alkylsulfonyl, C₁-C₈ haloalkylsulfonyl or C₃-C₈ cycloalkylsulfonyl.

Embodiment 62

A compound of Embodiment 61 wherein each R¹¹ is independently halogen,cyano, nitro, C₁-C₈ alkyl, C₁-C₄ cyanoalkyl, C₁-C₄ cyanoalkoxy, C₁-C₈haloalkyl, C₁-C₈ nitroalkyl, C₂-C₈ alkenyl, C₂-C₈ haloalkenyl, C₂-C₈nitroalkenyl, C₂-C₈ alkynyl, C₂-C₈ haloalkynyl, C₄-C₁₀ cycloalkylalkyl,C₄-C₁₀ halocycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₅-C₁₂cycloalkylalkenyl, C₅-C₁₂ cycloalkylalkynyl, C₃-C₈ cycloalkyl, C₁-C₈alkylsulfonyl, C₁-C₈ haloalkylsulfonyl or C₃-C₈ cycloalkylsulfonyl.

Embodiment 63

A compound of Embodiment 62 wherein each R¹¹ is independently halogen,C₁-C₈ alkyl, C₁-C₈ haloalkyl or C₁-C₈ alkylsulfonyl.

Embodiment 64

A compound of Embodiment 63 wherein each R¹¹ is independently F, Cl,CH₃, CF₃ or —SO₂CF₃.

Embodiment 65

A compound of Embodiment 64 wherein each R¹¹ is independently F, Cl,CH₃, CF₃ or —SO₂CF₃.

Embodiment 66

A compound of any one of Embodiments 1 through 65 wherein each R¹⁰ andR¹² is independently C₁-C₃ alkyl, C₃-C₆ cycloalkyl, C₂-C₃ alkoxyalkyl,C₂-C₃ alkylcarbonyl, C₂-C₃ alkoxycarbonyl or C₂-C₃ alkylaminoalkyl.

Embodiment 67

A compound of Embodiment 66 wherein each R¹⁰ and R¹² is independentlyC₁-C₃ alkyl, C₃-C₆ cycloalkyl or C₂-C₃ alkoxyalkyl.

Embodiment 68

A compound of Embodiment 67 wherein each R¹⁰ and R¹² is independentlyC₁-C₃ alkyl.

Embodiment 69

A compound of Embodiment 68 wherein each R¹⁰ and R¹² is independentlyCH₃.

Embodiment 70

A compound of Embodiment 1 wherein Q¹ is an 8- to 10-memberedheteroaromatic bicyclic ring system, each ring system containing ringmembers selected from carbon atoms and 1 to 4 heteroatoms independentlyselected from up to 2 O and up to 2 N atoms, wherein up to 3 carbon ringmembers are independently selected from C(═O) and C(═S), each ringsystem optionally substituted with up to 4 substituents independentlyselected from R⁹ on carbon atom ring members and selected from R¹⁰ onnitrogen atom ring members.

Embodiment 71

A compound of Embodiment 70 wherein Q¹ is an 8- to 9-memberedheteroaromatic bicyclic ring system, each ring system containing ringmembers selected from carbon atoms and 1 to 4 heteroatoms independentlyselected from up to 2 O atoms, each ring system optionally substitutedwith up to 4 substituents independently selected from R⁹ on carbon atomring members.

Embodiment 72

A compound of Embodiment 71 wherein Q¹ is an 9-membered heteroaromaticbicyclic ring system containing ring members selected from carbon atomsand 1 to 4 heteroatoms independently selected from up to 2 O atoms, eachring system optionally substituted with up to 4 substituentsindependently selected from R⁹ on carbon atom ring members.

Embodiment 73

A compound of Embodiment 72 wherein Q¹ is an 9-membered heteroaromaticbicyclic ring system containing ring members selected from carbon atomsand 2 O atoms, system optionally substituted with up to 3 substituentsindependently selected from R⁹ on carbon atom ring members (i.e. U-103in Exhibit 3).

Embodiment 74

A compound of Embodiment 73 wherein Q¹ is U-103A;

Embodiment 75

A compound of any one of Embodiments 1, 2 and 10 through 69 wherein Q¹is a phenyl ring optionally substituted with 1 to 4 substituentsindependently selected from R⁹; or a 5- to 6-membered heteroaromaticring containing ring members selected from carbon atoms and 1 to 4heteroatoms independently selected from up to 2 O, up to 2 S and up to 4N atoms, optionally substituted with up to 4 substituents independentlyselected from R⁹ on carbon atom ring members and selected from R¹⁰ onnitrogen atom ring members.

Embodiment 76

A compound of Embodiment 1 wherein Q² is a phenyl ring optionallysubstituted with up to 5 substituents independently selected from R¹¹;or a 5- to 6-membered fully unsaturated heterocyclic ring, each ringcontaining ring members selected from carbon atoms and 1 to 4heteroatoms independently selected from up to 2 O, up to 2 S and up to 4N atoms, each ring or ring system optionally substituted with up to 5substituents independently selected from R¹¹ on carbon atom ring membersand selected from R¹² on nitrogen atom ring members.

Embodiment 77

A compound of Embodiment 1 or 76 wherein Q² is a phenyl ring optionallysubstituted with up to 5 substituents independently selected from R¹¹;or a 6-membered fully unsaturated heterocyclic ring, each ringcontaining ring members selected from carbon atoms and 1 to 4heteroatoms independently selected from up to 4 N atoms, each ring orring system optionally substituted with up to 5 substituentsindependently selected from R¹¹ on carbon atom ring members.

Embodiment 78

A compound of Embodiment 77 wherein Q² is a phenyl ring optionallysubstituted with up to 4 substituents independently selected from R¹¹;or a pyridyl ring, optionally substituted with up to 4 substituentsindependently selected from R¹¹ on carbon atom ring members.

Embodiment 79

A compound of Embodiment 78 wherein Q² is a 3-pyridyl ring optionallysubstituted with up to 3 substituents independently selected from R¹¹ oncarbon atom ring members.

Embodiment 80

A compound of Embodiment 79 wherein Q² is a 3-pyridyl ring optionallysubstituted with up to 3 substituents independently selected from C₁-C₈alkyl or C₁-C₈ haloalkyl.

Embodiment 81

A compound of any one of Embodiments 1 through 56 or 60 through 80wherein each R⁹ is independently halogen, C₁-C₈ alkyl or C₁-C₈haloalkyl.

Embodiment 82

A compound of Embodiment 81 wherein each R⁹ is independently Cl, F, CH₃or CF₃.

Embodiment 83

A compound of Embodiment 82 wherein each R⁹ is independently CH₃.

Embodiment 84

A compound of any one of Embodiments 1 through 64 or 66 through 83wherein each R¹¹ is independently F, Cl, CH₃ or CF₃.

Embodiment 85

A compound of Embodiment 24 wherein A is —CH₂CH₂CH₂—, —CH═N—, —C(═O)CH₂—or —CH═CH— wherein the bond projecting to the left is connected tonitrogen of the —N-J- moiety, and the bond projecting to the right isconnected to the nitrogen of the —N═C— (or —N—CH—) moiety of Formula 1.

Embodiment 86

A compound of any one of Embodiments 1 through 24 or 30 through 84wherein A is —CH₂CH₂CH₂—, —CH═N—, —C(CH₃)═N—, —(CH₂CH₃)═N—,—C(CH₂CH₂CH₃)═N—, —C(CF₃)═N—, —C(═O)CH₂— or —CH═CH— wherein the bondprojecting to the left is connected to nitrogen of the —N-J- moiety, andthe bond projecting to the right is connected to the nitrogen of the—N═C— (or —N—CH—) moiety of Formula 1.

Embodiment 87

A compound of Embodiment 86 wherein A is —CH═N—, —C(CH₃)═N—,—C(CH₂CH₃)═N—, —C(CH₂CH₂CH₃)═N— or —C(CF₃)═N— wherein the bondprojecting to the left is connected to nitrogen of the —N-J- moiety, andthe bond projecting to the right is connected to the nitrogen of the—N═C— (or —N—CH—) moiety of Formula 1.

Embodiment 88

A compound of any one of Embodiments 1 through 24 or 30 through 84wherein A is —C(R³)═N— wherein the bond projecting to the left isconnected to nitrogen of the —N-J- moiety, and the bond projecting tothe right is connected to the nitrogen of the —N═C— (or —N—CH—) moietyof Formula 1.

Embodiment 89

A compound of Embodiment 88 wherein A is —CH═N—.

Embodiment 90

A compound of Embodiment 88 wherein A is —C(CH₃)═N—.

Embodiment 91

A compound of Embodiment 88 wherein A is —C(CH₂CH₃)═N—.

Embodiments of this invention, including Embodiments 1-91 above as wellas any other embodiments described herein, can be combined in anymanner, and the descriptions of variables in the embodiments pertain notonly to the compounds of Formula 1 but also to the starting compoundsand intermediate compounds useful for preparing the compounds ofFormula 1. In addition, embodiments of this invention, includingEmbodiments 1-91 above as well as any other embodiments describedherein, and any combination thereof, pertain to the compositions andmethods of the present invention.

Embodiment A

A compound of Formula 1 wherein:

-   -   Q¹ is a phenyl or benzyl ring or a naphthalenyl ring system,        each ring or ring system optionally substituted with up to 5        substituents independently selected from R⁹; or a 5- to        6-membered fully unsaturated heterocyclic ring, each ring or        ring system containing ring members selected from carbon atoms        and 1 to 4 heteroatoms independently selected from up to 2 O, up        to 2 S and up to 4 N atoms, wherein up to 3 carbon ring members        are independently selected from C(═O) and C(═S), and the sulfur        atom ring members are independently selected from        S(═O)_(u)(═NR⁸)_(v), each ring or ring system optionally        substituted with up to 5 substituents independently selected        from R⁹ on carbon atom ring members and selected from R¹⁰ on        nitrogen atom ring members;    -   Q² is a phenyl ring or a naphthalenyl ring system, each ring or        ring system optionally substituted with up to 5 substituents        independently selected from R¹¹; or a 5- to 6-membered fully        unsaturated heterocyclic ring, each ring containing ring members        selected from carbon atoms and 1 to 4 heteroatoms independently        selected from up to 1 O, up to 1 S and up to 2 N atoms, wherein        up to 2 carbon ring members are independently selected from        C(═O) and C(═S), and the sulfur atom ring members are        independently selected from S(═O)_(u)(═NR⁸)_(v), each ring or        ring system optionally substituted with up to 5 substituents        independently selected from R¹¹ on carbon atom ring members and        selected from R¹² on nitrogen atom ring members;    -   R¹ and R² are each independently H, halogen or C₁-C₄ alkyl;    -   Y is O or S;    -   A is a saturated, partially unsaturated or fully unsaturated        chain containing 2 to 4 atoms selected from up to 3 carbon, up        to 1 O, up to 1 S and up to 1 N atoms, wherein up to 2 carbon        members are independently selected from C(═O) and C(═S) and the        sulfur atom member is selected from S(═O)_(u)(═NR⁸)_(v); the        said chain optionally substituted with up to 3 substituents        independently selected from R³ on carbon atoms and R⁴ on        nitrogen atoms;    -   each R³ is independently halogen, cyano, hydroxy, —CO₂H, C₁-C₄        alkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy, C₁-C₄ alkylthio, C₃-C₆        cycloalkyl or C₄-C₆ cycloalkylalkyl;    -   each R⁴ is independently C₁-C₄ alkyl, C₁-C₄ haloalkyl or C₃-C₆        cycloalkyl;    -   R⁵ and R⁶ are each independently H, halogen, hydroxy or CH₃;    -   R^(5a) and R^(6a) are each independently H or C₁-C₄ alkyl;    -   R⁷ is H, hydroxy, amino, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆        alkenyl, C₃-C₆ alkynyl, C₂-C₈ alkoxyalkyl, C₂-C₈        haloalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl,        C₂-C₈ alkylsulfonylalkyl, C₂-C₈ alkylcarbonyl, C₂-C₈        haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, C₂-C₈        alkoxycarbonyl, C₂-C₈ haloalkoxycarbonyl, C₄-C₁₀        cycloalkoxycarbonyl, C₂-C₈ alkylaminocarbonyl, C₃-C₁₀        dialkylaminocarbonyl or C₄-C₁₀ cycloalkylaminocarbonyl;    -   each R⁸ is independently H, cyano or C₂-C₃ alkylcarbonyl;    -   each R⁹ is independently halogen, cyano, nitro, C₁-C₈ alkyl,        C₁-C₄ cyanoalkyl, C₁-C₄ cyanoalkoxy, C₁-C₈ haloalkyl, C₁-C₈        nitroalkyl, C₂-C₈ alkenyl, C₂-C₈ haloalkenyl, C₂-C₈        nitroalkenyl, C₂-C₈ alkynyl, C₂-C₈ haloalkynyl, C₄-C₁₀        cycloalkylalkyl, C₄-C₁₀ halocycloalkylalkyl, C₅-C₁₂        alkylcycloalkylalkyl, C₅-C₁₂ cycloalkylalkenyl, C₅-C₁₂        cycloalkylalkynyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl,        C₄-C₁₀ alkylcycloalkyl, C₆-C₁₂ cycloalkylcycloalkyl, C₃-C₈        cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₂-C₈        haloalkoxyalkyl, C₃-C₈ haloalkoxyalkoxy, C₁-C₄ hydroxyalkyl,        C₄-C₁₀ cycloalkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈        alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈        alkylsulfonylalkyl, C₂-C₈ alkylaminoalkyl, C₂-C₈        haloalkylaminoalkyl, C₄-C₁₀ cycloalkylaminoalkyl, C₃-C₁₀        dialkylaminoalkyl, —CHO, C₂-C₈ alkylcarbonyl, C₂-C₈        haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, —C(═O)OH, C₂-C₈        alkoxycarbonyl, C₂-C₈ haloalkoxycarbonyl, C₄-C₁₀        cycloalkoxycarbonyl, C₅-C₁₂ cycloalkylalkoxycarbonyl, —C(═O)NH₂,        C₂-C₈ alkylaminocarbonyl, C₄-C₁₀ cycloalkylaminocarbonyl, C₃-C₁₀        dialkylaminocarbonyl, C₁-C₈ alkoxy, C₁-C₈ haloalkoxy, C₂-C₈        alkoxyalkoxy, C₂-C₈ alkenyloxy, C₂-C₈ haloalkenyloxy, C₂-C₈        haloalkoxyhaloalkoxy, C₃-C₈ alkynyloxy, C₃-C₈ haloalkynyloxy,        C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₄-C₁₀        cycloalkylalkoxy, C₃-C₁₀ alkylcarbonylalkoxy, C₂-C₈        alkylcarbonyloxy, C₂-C₈ haloalkylcarbonyloxy or C₄-C₁₀        cycloalkylcarbonyloxy;    -   each R¹¹ is independently halogen, cyano, nitro, C₁-C₈ alkyl,        C₁-C₄ cyanoalkyl, C₁-C₄ cyanoalkoxy, C₁-C₈ haloalkyl, C₁-C₈        nitroalkyl, C₂-C₈ alkenyl, C₂-C₈ haloalkenyl, C₂-C₈        nitroalkenyl, C₂-C₈ alkynyl, C₂-C₈ haloalkynyl, C₄-C₁₀        cycloalkylalkyl, C₄-C₁₀ halocycloalkylalkyl, C₅-C₁₂        alkylcycloalkylalkyl, C₅-C₁₂ cycloalkylalkenyl, C₅-C₁₂        cycloalkylalkynyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl,        C₄-C₁₀ alkylcycloalkyl, C₆-C₁₂ cycloalkylcycloalkyl, C₃-C₈        cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₂-C₈        haloalkoxyalkyl, C₃-C₈ haloalkoxyalkoxy, C₁-C₄ hydroxyalkyl,        C₄-C₁₀ cycloalkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈        alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈        alkylsulfonylalkyl, C₂-C₈ alkylaminoalkyl, C₂-C₈        haloalkylaminoalkyl, C₄-C₁₀ cycloalkylaminoalkyl, C₃-C₁₀        dialkylaminoalkyl, —CHO, C₂-C₈ alkylcarbonyl, C₂-C₈        haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, —C(═O)OH, C₂-C₈        alkoxycarbonyl, C₂-C₈ haloalkoxycarbonyl, C₄-C₁₀        cycloalkoxycarbonyl, C₅-C₁₂ cycloalkylalkoxycarbonyl, —C(═O)NH₂,        C₂-C₈ alkylaminocarbonyl, C₄-C₁₀ cycloalkylaminocarbonyl, C₃-C₁₀        dialkylaminocarbonyl, C₁-C₈ alkoxy, C₁-C₈ haloalkoxy, C₂-C₈        alkoxyalkoxy, C₂-C₈ alkenyloxy, C₂-C₈ haloalkenyloxy, C₂-C₈        haloalkoxyhaloalkoxy, C₃-C₈ alkynyloxy, C₃-C₈ haloalkynyloxy,        C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₄-C₁₀        cycloalkylalkoxy, C₃-C₁₀ alkylcarbonylalkoxy, C₂-C₈        alkylcarbonyloxy, C₂-C₈ haloalkylcarbonyloxy, C₄-C₁₀        cycloalkylcarbonyloxy, C₁-C₈ alkylsulfonyloxy, C₁-C₈        haloalkylsulfonyloxy, C₁-C₈ alkylthio, C₁-C₈ haloalkylthio,        C₃-C₈ cycloalkylthio, C₁-C₈ alkylsulfinyl, C₁-C₈        haloalkylsulfinyl, C₁-C₈ alkyl sulfonyl, C₁-C₈        haloalkylsulfonyl, C₃-C₈ cycloalkylsulfonyl, formylamino, C₂-C₈        alkylcarbonylamino, C₂-C₈ haloalkylcarbonylamino or C₂-C₈        alkoxycarbonylamino; and    -   each R¹⁰ and R¹² is independently C₁-C₃ alkyl, C₃-C₆ cycloalkyl,        C₂-C₃ alkoxyalkyl, C₂-C₃ alkylcarbonyl, C₂-C₃ alkoxycarbonyl or        C₂-C₃ alkylaminoalkyl.

Embodiment B

A compound of Embodiment A wherein

-   -   Q¹ is a phenyl ring optionally substituted with up to 5        substituents independently selected from R⁹; or a 5- to        6-membered fully unsaturated heterocyclic ring, each ring        containing ring members selected from carbon atoms and 1 to 4        heteroatoms independently selected from up to 2 O, up to 2 S and        up to 4 N atoms, wherein up to 3 carbon ring members are        independently selected from C(═O) and C(═S), and the sulfur atom        ring members are independently selected from        S(═O)_(u)(═NR⁸)_(v), each ring or ring system optionally        substituted with up to 5 substituents independently selected        from R⁹ on carbon atom ring members and selected from R¹⁰ on        nitrogen atom ring members;    -   Q² is a phenyl ring optionally substituted with up to 5        substituents independently selected from R¹¹;    -   R¹ and R² are each independently H, Cl, or CH₃;    -   Y is O;    -   A is a saturated or partially unsaturated chain containing 2 to        4 atoms selected from up to 2 carbon and up to 1 N atoms,        wherein up to 1 carbon member is independently selected from        C(═O) and C(═S); the said chain optionally substituted with up        to 2 substituents independently selected from R³ on carbon atoms        and R⁴ on nitrogen atoms;    -   each R³ is independently cyano, —CO₂H, C₁-C₄ alkyl, C₁-C₄        haloalkyl, C₁-C₄ alkylthio or C₄-C₆ cycloalkylalkyl;    -   each R⁴ is independently C₁-C₄ alkyl;    -   J is —CR⁵R⁶—;    -   R⁵ and R⁶ are each independently H or halogen;    -   R⁷ is H, hydroxy, amino, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆        alkenyl, C₃-C₆ alkynyl, C₂-C₈ alkoxyalkyl, C₂-C₈ haloalkoxyalkyl        or C₂-C₈ alkylthioalkyl;    -   each R⁸ is independently H;    -   each R⁹ is independently halogen, cyano, nitro, C₁-C₈ alkyl,        C₁-C₄ cyanoalkyl, C₁-C₄ cyanoalkoxy, C₁-C₈ haloalkyl, C₁-C₈        nitroalkyl, C₂-C₈ alkenyl, C₂-C₈ haloalkenyl, C₂-C₈        nitroalkenyl, C₂-C₈ alkynyl, C₂-C₈ haloalkynyl, C₄-C₁₀        cycloalkylalkyl, C₄-C₁₀ halocycloalkylalkyl, C₅-C₁₂        alkylcycloalkylalkyl, C₅-C₁₂ cycloalkylalkenyl, C₅-C₁₂        cycloalkylalkynyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl,        C₄-C₁₀ alkylcycloalkyl, C₆-C₁₂ cycloalkylcycloalkyl, C₃-C₈        cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₂-C₈        haloalkoxyalkyl, C₃-C₈ haloalkoxyalkoxy, C₁-C₄ hydroxyalkyl,        C₄-C₁₀ cycloalkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈        alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈        alkylsulfonylalkyl, C₂-C₈ alkylaminoalkyl, C₂-C₈        haloalkylaminoalkyl, C₄-C₁₀ cycloalkylaminoalkyl or C₃-C₁₀        dialkylaminoalkyl;    -   each R¹¹ is independently halogen, cyano, nitro, C₁-C₈ alkyl,        C₁-C₄ cyanoalkyl, C₁-C₄ cyanoalkoxy, C₁-C₈ haloalkyl, C₁-C₈        nitroalkyl, C₂-C₈ alkenyl, C₂-C₈ haloalkenyl, C₂-C₈        nitroalkenyl, C₂-C₈ alkynyl, C₂-C₈ haloalkynyl, C₄-C₁₀        cycloalkylalkyl, C₄-C₁₀ halocycloalkylalkyl, C₅-C₁₂        alkylcycloalkylalkyl, C₅-C₁₂ cycloalkylalkenyl, C₅-C₁₂        cycloalkylalkynyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl,        C₄-C₁₀ alkylcycloalkyl, C₆-C₁₂ cycloalkylcycloalkyl, C₃-C₈        cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₂-C₈        haloalkoxyalkyl, C₃-C₈ haloalkoxyalkoxy, C₁-C₄ hydroxyalkyl,        C₄-C₁₀ cycloalkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈        alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈        alkylsulfonylalkyl, C₁-C₈ alkylsulfonyloxy, C₁-C₈        haloalkylsulfonyloxy, C₁-C₈ alkylthio, C₁-C₈ haloalkylthio,        C₃-C₈ cycloalkylthio, C₁-C₈ alkylsulfinyl, C₁-C₈        haloalkylsulfinyl, C₁-C₈ alkylsulfonyl, C₁-C₈ haloalkylsulfonyl        or C₃-C₈ cycloalkylsulfonyl; and    -   each R¹⁰ and R¹² is independently C₁-C₃ alkyl, C₃-C₆ cycloalkyl        or C₂-C₃ alkoxyalkyl.

Embodiment C

A compound of Embodiment B wherein

-   -   Q¹ is a phenyl ring optionally substituted with up to 5        substituents independently selected from R⁹;    -   Q² is a phenyl ring optionally substituted with up to 3        substituents independently selected from R¹¹;    -   R¹ and R² are each independently H or Cl;    -   A is a saturated or partially unsaturated chain containing 2 to        3 atoms selected from up to 2 carbon and up to 1 N atoms,        wherein up to 1 carbon member is independently selected from        C(═O); the said chain optionally substituted with up to 1        substituent independently selected from R³ on carbon atoms and        R⁴ on nitrogen atoms;    -   each R³ is independently cyano, —CO₂H or C₁-C₄ alkyl;    -   each R⁴ is CH₃;    -   R⁵ and R⁶ are each independently H or halogen;    -   R⁷ is H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₃-C₆ alkynyl or C₂-C₈        alkoxyalkyl;    -   each R⁹ is independently halogen, cyano, nitro, C₁-C₈ alkyl,        C₁-C₄ cyanoalkyl, C₁-C₄ cyanoalkoxy, C₁-C₈ haloalkyl, C₁-C₈        nitroalkyl, C₂-C₈ alkenyl, C₂-C₈ haloalkenyl, C₂-C₈        nitroalkenyl, C₂-C₈ alkynyl, C₂-C₈ haloalkynyl, C₄-C₁₀        cycloalkylalkyl, C₄-C₁₀ halocycloalkylalkyl, C₅-C₁₂        alkylcycloalkylalkyl, C₅-C₁₂ cycloalkylalkenyl, C₅-C₁₂        cycloalkylalkynyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl,        C₄-C₁₀ alkylcycloalkyl or C₆-C₁₂ cycloalkylcycloalkyl; and    -   each R¹¹ is independently halogen, cyano, nitro, C₁-C₈ alkyl,        C₁-C₄ cyanoalkyl, C₁-C₄ cyanoalkoxy, C₁-C₈ haloalkyl, C₁-C₈        nitroalkyl, C₂-C₈ alkenyl, C₂-C₈ haloalkenyl, C₂-C₈        nitroalkenyl, C₂-C₈ alkynyl, C₂-C₈ haloalkynyl, C₄-C₁₀        cycloalkylalkyl, C₄-C₁₀ halocycloalkylalkyl, C₅-C₁₂        alkylcycloalkylalkyl, C₅-C₁₂ cycloalkylalkenyl, C₅-C₁₂        cycloalkylalkynyl, C₃-C₈ cycloalkyl, C₁-C₈ alkylsulfonyl, C₁-C₈        haloalkylsulfonyl or C₃-C₈ cycloalkylsulfonyl.

Embodiment D

A compound of Embodiment C wherein

-   -   Q¹ is a phenyl ring substituted with 1 to 3 substituents        independently selected from R⁹;    -   Q² is a phenyl ring substituted with 1 substituent independently        selected from R¹¹ at the 3-position;    -   R¹ and R² are each H;    -   A is —CH₂CH₂CH₂—, —NCH₂—, —C(═O)CH₂— or —CH═CH— wherein the bond        projecting to the left is connected to nitrogen of the —N-J-        moiety, and the bond projecting to the right is connected to the        nitrogen of the —N═C— moiety of Formula 1;    -   each R⁹ is independently halogen, cyano, nitro, C₁-C₈ alkyl,        C₁-C₄ cyanoalkyl, C₁-C₄ cyanoalkoxy or C₁-C₈ haloalkyl; and    -   each R¹¹ is independently halogen, C₁-C₈ alkyl, C₁-C₈ haloalkyl        or C₁-C₈ alkylsulfonyl.

Embodiment E

A compound of Embodiment D wherein

-   -   Q¹ is a phenyl ring substituted with 1 to 2 substituents        independently selected from R⁹;    -   A is CH₂CH₂CH₂;    -   each R⁹ is independently halogen or C₁-C₈ haloalkyl; and    -   each R¹¹ is independently F, Cl, CH₃, CF₃ or SO₂CF₃.

Embodiment F

A compound of Embodiment D wherein

-   -   Q¹ is a phenyl ring substituted with 1 to 2 substituents        independently selected from R⁹;    -   A is —NCH₂— wherein the bond projecting to the left is connected        to nitrogen of the —N-J- moiety, and the bond projecting to the        right is connected to the nitrogen of the —N═C— moiety of        Formula 1;    -   each R⁹ is independently F, Cl, CF₃; and    -   each R¹¹ is independently F, Cl, CH₃, CF₃ or —SO₂CF₃.

Embodiment G

A compound of Embodiment C wherein

-   -   A is —CH₂CH₂CH₂—, —CH═N—, —C(CH₃)═N—, —(CH₂CH₃)═N—,        —C(CH₂CH₂CH₃)═N—, —C(CF₃)═N—, —C(═O)CH₂— or —CH═CH— wherein the        bond projecting to the left is connected to nitrogen of the        —N-J- moiety, and the bond projecting to the right is connected        to the nitrogen of the —N═C— (or —N—CH—) moiety of Formula 1;    -   each R⁹ is independently halogen, cyano, nitro, C₁-C₈ alkyl,        C₁-C₄ cyanoalkyl, C₁-C₄ cyanoalkoxy or C₁-C₈ haloalkyl; and    -   each R¹¹ is independently halogen, C₁-C₈ alkyl, C₁-C₈ haloalkyl        or C₁-C₈ alkyl sulfonyl.

Embodiment H

A compound of Embodiment G wherein

-   -   A is —CH═N—, —C(CH₃)═N—, —C(CH₂CH₃)═N—, —C(CH₂CH₂CH₃)═N— or        —C(CF₃)═N— wherein the bond projecting to the left is connected        to nitrogen of the —N-J- moiety, and the bond projecting to the        right is connected to the nitrogen of the —N═C— (or —N—CH—)        moiety of Formula 1;    -   each R⁹ is independently halogen, C₁-C₈ alkyl or C₁-C₈        haloalkyl; and    -   each R¹¹ is independently F, Cl, CH₃ or CF₃.        Specific Embodiments of the Invention include a compound of the        Summary of the Invention selected from:

-   N-(2-fluorophenyl)-6,7-dihydro-6-[3-(trifluoromethyl)phenyl]-5H-pyrrolo[2,1-c]-1,2,4-triazole-7-carboxamide;    and

-   N-(2-fluorophenyl)-2,3,6,7-tetrahydro-3-oxo-6-[3-(trifluoromethyl)pheny]-5H-pyrrolo[1,2-a]imidazole-7-carboxamide.

This invention also relates to a method for controlling undesiredvegetation comprising applying to the locus of the vegetationherbicidally effective amounts of the compounds of the invention (e.g.,as a composition described herein). Of note as embodiments relating tomethods of use are those involving the compounds of embodimentsdescribed above. Compounds of the invention are particularly useful forselective control of broadleaf weeds in crops such as wheat, barley,maize, soybean, sunflower, cotton, oilseed rape and rice, and specialtycrops such as sugarcane, citrus, fruit and nut crops.

Also noteworthy as embodiments are herbicidal compositions of thepresent invention comprising the compounds of embodiments describedabove.

This invention also includes a herbicidal mixture comprising (a) acompound selected from Formula 1, N-oxides, and salts thereof, and (b)at least one additional active ingredient selected from (b1) photosystemII inhibitors, (b2) acetohydroxy acid synthase (AHAS) inhibitors, (b3)acetyl-CoA carboxylase (ACCase) inhibitors, (b4) auxin mimics, (b5)5-enol-pyruvylshikimate-3-phosphate (EPSP) synthase inhibitors, (b6)photosystem I electron diverters, (b7) protoporphyrinogen oxidase (PPO)inhibitors, (b8) glutamine synthetase (GS) inhibitors, (b9) very longchain fatty acid (VLCFA) elongase inhibitors, (b10) auxin transportinhibitors, (b11) phytoene desaturase (PDS) inhibitors, (b12)4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors, (b13)homogentisate solenesyltransererase (HST) inhibitors, (b14) cellulosebiosynthesis inhibitors, (b15) other herbicides including mitoticdisruptors, organic arsenicals, asulam, bromobutide, cinmethylin,cumyluron, dazomet, difenzoquat, dymron, etobenzanid, flurenol,fosamine, fosamine-ammonium, hydantocidin, metam, methyldymron, oleicacid, oxaziclomefone, pelargonic acid and pyributicarb, and (b16)herbicide safeners; and salts of compounds of (b1) through (b16).

“Photosystem II inhibitors” (b1) are chemical compounds that bind to theD-1 protein at the Q_(B)-binding niche and thus block electron transportfrom Q_(A) to Q_(B) in the chloroplast thylakoid membranes. Theelectrons blocked from passing through photosystem II are transferredthrough a series of reactions to form toxic compounds that disrupt cellmembranes and cause chloroplast swelling, membrane leakage, andultimately cellular destruction. The Q_(B)-binding niche has threedifferent binding sites: binding site A binds the triazines such asatrazine, triazinones such as hexazinone, and uracils such as bromacil,binding site B binds the phenylureas such as diuron, and binding site Cbinds benzothiadiazoles such as bentazon, nitriles such as bromoxyniland phenyl-pyridazines such as pyridate. Examples of photosystem IIinhibitors include ametryn, amicarbazone, atrazine, bentazon, bromacil,bromofenoxim, bromoxynil, chlorbromuron, chloridazon, chlorotoluron,chloroxuron, cumyluron, cyanazine, daimuron, desmedipham, desmetryn,dimefuron, dimethametryn, diuron, ethidimuron, fenuron, fluometuron,hexazinone, ioxynil, isoproturon, isouron, lenacil, linuron, metamitron,methabenzthiazuron, metobromuron, metoxuron, metribuzin, monolinuron,neburon, pentanochlor, phenmedipham, prometon, prometryn, propanil,propazine, pyridafol, pyridate, siduron, simazine, simetryn,tebuthiuron, terbacil, terbumeton, terbuthylazine, terbutryn andtrietazine. Of note is a compound of the invention mixed with atrazine,bromoxynil or metribuzin.

“AHAS inhibitors” (b2) are chemical compounds that inhibit acetohydroxyacid synthase (AHAS), also known as acetolactate synthase (ALS), andthus kill plants by inhibiting the production of the branched-chainaliphatic amino acids such as valine, leucine and isoleucine, which arerequired for protein synthesis and cell growth. Examples of AHASinhibitors include amidosulfuron, azimsulfuron, bensulfuron-methyl,bispyribac-sodium, cloransulam-methyl, chlorimuron-ethyl, chlorsulfuron,cinosulfuron, cyclosulfamuron, diclosulam, ethametsulfuron-methyl,ethoxysulfuron, flazasulfuron, florasulam, flucarbazone-sodium,flumetsulam, flupyrsulfuron-methyl, flupyrsulfuron-sodium,foramsulfuron, halosulfuron-methyl, imazamethabenz-methyl, imazamox,imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron,iodosulfuron-methyl (including sodium salt), iofensulfuron(2-iodo-N-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]benzenesulfonamide),mesosulfuron-methyl, metazosulfuron(3-chloro-4-(5,6-dihydro-5-methyl-1,4,2-dioxazin-3-yl)-N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-1-methyl-1H-pyrazole-5-sulfonamide),metosulam, metsulfuron-methyl, nicosulfuron, oxasulfuron, penoxsulam,primisulfuron-methyl, propoxycarbazone-sodium, propyrisulfuron(2-chloro-N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-6-propylimidazo[1,2-b]pyridazine-3-sulfonamide),prosulfuron, pyrazosulfuron-ethyl, pyribenzoxim, pyriftalid,pyriminobac-methyl, pyrithiobac-sodium, rimsulfuron,sulfometuron-methyl, sulfosulfuron, thiencarbazone,thifensulfuron-methyl, triafamone(N-[2-[(4,6-dimethoxy-1,3,5-triazin-2-yl)carbonyl]-6-fluorophenyl]-1,1-difluoro-N-methylmethanesulfonamide),triasulfuron, tribenuron-methyl, trifloxysulfuron (including sodiumsalt), triflusulfuron-methyl and tritosulfuron. Of note is a compound ofthe invention mixed with nicosulfuron, flupyrsulfuron or chlorimuron.

“ACCase inhibitors” (b3) are chemical compounds that inhibit theacetyl-CoA carboxylase enzyme, which is responsible for catalyzing anearly step in lipid and fatty acid synthesis in plants. Lipids areessential components of cell membranes, and without them, new cellscannot be produced. The inhibition of acetyl CoA carboxylase and thesubsequent lack of lipid production leads to losses in cell membraneintegrity, especially in regions of active growth such as meristems.Eventually shoot and rhizome growth ceases, and shoot meristems andrhizome buds begin to die back. Examples of ACCase inhibitors includealloxydim, butroxydim, clethodim, clodinafop, cycloxydim, cyhalofop,diclofop, fenoxaprop, fluazifop, haloxyfop, pinoxaden, profoxydim,propaquizafop, quizalofop, sethoxydim, tepraloxydim and tralkoxydim,including resolved forms such as fenoxaprop-P, fluazifop-P, haloxyfop-Pand quizalofop-P and ester forms such as clodinafop-propargyl,cyhalofop-butyl, diclofop-methyl and fenoxaprop-P-ethyl. Of note is acompound of the invention mixed with pinoxaden or quizalofop.

Auxin is a plant hormone that regulates growth in many plant tissues.“Auxin mimics” (b4) are chemical compounds mimicking the plant growthhormone auxin, thus causing uncontrolled and disorganized growth leadingto plant death in susceptible species. Examples of auxin mimics includeaminocyclopyrachlor(6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid) and itsmethyl and ethyl esters and its sodium and potassium salts,aminopyralid, benazolin-ethyl, chloramben, clacyfos, clomeprop,clopyralid, dicamba, 2,4-D, 2,4-DB, dichlorprop, fluroxypyr, halauxifen(4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-2-pyridinecarboxylicacid), halauxifen-methyl (methyl4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-2-pyridinecarboxylate),MCPA, MCPB, mecoprop, picloram, quinclorac, quinmerac, 2,3,6-TBA,triclopyr, and methyl4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylate.Of note is a compound of the invention mixed with dicamba.

“EPSP synthase inhibitors” (b5) are chemical compounds that inhibit theenzyme, 5-enol-pyruvylshikimate-3-phosphate synthase, which is involvedin the synthesis of aromatic amino acids such as tyrosine, tryptophanand phenylalanine. EPSP inhibitor herbicides are readily absorbedthrough plant foliage and translocated in the phloem to the growingpoints. Glyphosate is a relatively nonselective postemergence herbicidethat belongs to this group. Glyphosate includes esters and salts such asammonium, isopropylammonium, potassium, sodium (including sesquisodium)and trimesium (alternatively named sulfosate).

“Photosystem I electron diverters” (b6) are chemical compounds thataccept electrons from Photosystem I, and after several cycles, generatehydroxyl radicals. These radicals are extremely reactive and readilydestroy unsaturated lipids, including membrane fatty acids andchlorophyll. This destroys cell membrane integrity, so that cells andorganelles “leak”, leading to rapid leaf wilting and desiccation, andeventually to plant death. Examples of this second type ofphotosynthesis inhibitor include diquat and paraquat.

“PPO inhibitors” (b7) are chemical compounds that inhibit the enzymeprotoporphyrinogen oxidase, quickly resulting in formation of highlyreactive compounds in plants that rupture cell membranes, causing cellfluids to leak out. Examples of PPO inhibitors includeacifluorfen-sodium, azafenidin, benzfendizone, bifenox, butafenacil,carfentrazone, carfentrazone-ethyl, chlomethoxyfen, cinidon-ethyl,fluazolate, flufenpyr-ethyl, flumiclorac-pentyl, flumioxazin,fluoroglycofen-ethyl, fluthiacet-methyl, fomesafen, halosafen, lactofen,oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil,pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimin,trifludimoxazin(dihydro-1,5-dimehyl-6-thioxo-3-[2,2,7-trifluoro-3,4-dihydro-3-oxo-4-(2-propyn-1-yl)-2H-1,4-benzoxazin-6-yl]-1,3,5-triazine-2,4(1H,3H)-dione)and tiafenacil (methylN-[2-[[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl]thio]-1-oxopropyl]-β-alaninate).

“GS inhibitors” (b8) are chemical compounds that inhibit the activity ofthe glutamine synthetase enzyme, which plants use to convert ammoniainto glutamine. Consequently, ammonia accumulates and glutamine levelsdecrease. Plant damage probably occurs due to the combined effects ofammonia toxicity and deficiency of amino acids required for othermetabolic processes. The GS inhibitors include glufosinate and itsesters and salts such as glufosinate-ammonium and other phosphinothricinderivatives, glufosinate-P((2S)-2-amino-4-(hydroxymethylphosphinyl)butanoic acid) and bilanaphos.

“VLCFA elongase inhibitors” (b9) are herbicides having a wide variety ofchemical structures, which inhibit the elongase. Elongase is one of theenzymes located in or near chloroplasts which are involved inbiosynthesis of VLCFAs. In plants, very-long-chain fatty acids are themain constituents of hydrophobic polymers that prevent desiccation atthe leaf surface and provide stability to pollen grains. Such herbicidesinclude acetochlor, alachlor, anilofos, butachlor, cafenstrole,dimethachlor, dimethenamid, diphenamid, fenoxasulfone(3-[[(2,5-dichloro-4-ethoxyphenyl)methyl]sulfonyl]-4,5-dihydro-5,5-dimethylisoxazole),fentrazamide, flufenacet, indanofan, mefenacet, metazachlor,metolachlor, naproanilide, napropamide, napropamide-M((2R)—N,N-diethyl-2-(1-naphthalenyloxy)propanamide), pethoxamid,piperophos, pretilachlor, propachlor, propisochlor, pyroxasulfone, andthenylchlor, including resolved forms such as S-metolachlor andchloroacetamides and oxyacetamides. Of note is a compound of theinvention mixed with flufenacet.

“Auxin transport inhibitors” (b10) are chemical substances that inhibitauxin transport in plants, such as by binding with an auxin-carrierprotein. Examples of auxin transport inhibitors include diflufenzopyr,naptalam (also known as N-(1-naphthyl)phthalamic acid and2-[(1-naphthalenylamino)carbonyl]benzoic acid).

“PDS inhibitors” (b11) are chemical compounds that inhibit carotenoidbiosynthesis pathway at the phytoene desaturase step. Examples of PDSinhibitors include beflubutamid, diflufenican, fluridone,flurochloridone, flurtamone norflurzon and picolinafen.

“HPPD inhibitors” (b12) are chemical substances that inhibit thebiosynthesis of synthesis of 4-hydroxyphenyl-pyruvate dioxygenase.Examples of HPPD inhibitors include benzobicyclon, benzofenap,bicyclopyrone(4-hydroxy-3-[[2-[(2-methoxyethoxy)methyl]-6-(trifluoromethyl)-3-pyridinyl]carbonyl]bicyclo[3.2.1]oct-3-en-2-one),fenquinotrione(2-[[8-chloro-3,4-dihydro-4-(4-methoxyphenyl)-3-oxo-2-quinoxalinyl]carbonyl]-1,3-cyclohexanedione),isoxachlortole, isoxaflutole, mesotrione, pyrasulfotole, pyrazolynate,pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate(1-[[1-ethyl-4-[3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoyl]-1H-pyrazol-5-yl]oxy]ethylmethyl carbonate), topramezone,5-chloro-3-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-1-(4-methoxyphenyl)-2(1H)-quinoxalinone,4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone,4-(4-fluorophenyl)-6-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-methyl-1,2,4-triazine-3,5(2H,4H)-dione,5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-(3-methoxyphenyl)-3-(3-methoxypropyl)-4(3H)-pyrimidinone,2-methyl-N-(4-methyl-1,2,5-oxadiazol-3-yl)-3-(methylsulfinyl)-4-(trifluoromethyl)benzamideand2-methyl-3-(methylsulfonyl)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide.Of note is a compound of the invention mixed with mesotrione orpyrasulfatole.

“HST inhibitors” (b13) disrupt a plant's ability to converthomogentisate to 2-methyl-6-solanyl-1,4-benzoquinone, thereby disruptingcarotenoid biosynthesis. Examples of HST inhibitors include haloxydine,pyriclor, cyclopyrimorate(6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-morpholinecarboxylate),3-(2-chloro-3,6-difluorophenyl)-4-hydroxy-1-methyl-1,5-naphthyridin-2(1H)-one,7-(3,5-dichloro-4-pyridinyl)-5-(2,2-difluoroethyl)-8-hydroxypyrido[2,3-b]pyrazin-6(5H)-oneand4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone.

HST inhibitors also include compounds of Formulae A and B.

-   -   wherein R^(d1) is H, Cl or CF₃; R^(d2) is H, Cl or Br; R^(d3) is        H or Cl; R^(d4) is H, Cl or CF₃; R^(d5) is CH₃, CH₂CH₃ or        CH₂CHF₂; and R^(d6) is OH, or —OC(═O)-i-Pr; and R^(e1) is H, F,        Cl, CH₃ or CH₂CH₃; R^(e2) is H or CF₃; R^(e3) is H, CH₃ or        CH₂CH₃; R^(e4) is H, F or Br; R^(e5) is Cl, CH₃, CF₃, OCF₃ or        CH₂CH₃; R^(e6) is H, CH₃, CH₂CHF₂ or C≡CH; R^(e7) is OH,        —OC(═O)Et, —OC(═O)-i-Pr or —OC(═O)-t-Bu; and A^(e8) is N or CH.

“Cellulose biosynthesis inhibitors” (b14) inhibit the biosynthesis ofcellulose in certain plants. They are most effective when appliedpreemergence or early postemergence on young or rapidly growing plants.Examples of cellulose biosynthesis inhibitors include chlorthiamid,dichlobenil, flupoxam, indaziflam(N²-[(1R,2S)-2,3-dihydro-2,6-dimethyl-1H-inden-1-yl]-6-(1-fluoroethyl)-1,3,5-triazine-2,4-diamine),isoxaben and triaziflam.

“Other herbicides” (b15) include herbicides that act through a varietyof different modes of action such as mitotic disruptors (e.g.,flamprop-M-methyl and flamprop-M-isopropyl), organic arsenicals (e.g.,DSMA, and MSMA), 7,8-dihydropteroate synthase inhibitors, chloroplastisoprenoid synthesis inhibitors and cell-wall biosynthesis inhibitors.Other herbicides include those herbicides having unknown modes of actionor do not fall into a specific category listed in (b1) through (b14) oract through a combination of modes of action listed above. Examples ofother herbicides include aclonifen, asulam, amitrole, bromobutide,cinmethylin, clomazone, cumyluron, daimuron, difenzoquat, etobenzanid,fluometuron, flurenol, fosamine, fosamine-ammonium, dazomet, dymron,ipfencarbazone(1-(2,4-dichlorophenyl)-N-(2,4-difluorophenyl)-1,5-dihydro-N-(1-methylethyl)-5-oxo-4H-1,2,4-triazole-4-carboxamide),metam, methyldymron, oleic acid, oxaziclomefone, pelargonic acid,pyributicarb and5-[[(2,6-difluorophenyl)methoxy]methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)isoxazole.

“Herbicide safeners” (b16) are substances added to a herbicideformulation to eliminate or reduce phytotoxic effects of the herbicideto certain crops. These compounds protect crops from injury byherbicides but typically do not prevent the herbicide from controllingundesired vegetation. Examples of herbicide safeners include but are notlimited to benoxacor, cloquintocet-mexyl, cumyluron, cyometrinil,cyprosulfamide, daimuron, dichlormid, dicyclonon, dietholate,dimepiperate, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim,furilazole, isoxadifen-ethyl, mefenpyr-diethyl, mephenate,methoxyphenone, naphthalic anhydride, oxabetrinil,N-(aminocarbonyl)-2-methylbenzenesulfonamide andN-(aminocarbonyl)-2-fluorobenzenesulfonamide,1-bromo-4-[(chloromethyl)sulfonyl]benzene,2-(dichloromethyl)-2-methyl-1,3-dioxolane (MG 191),4-(dichloroacetyl)-1-oxa-4-azospiro[4.5]decane (MON 4660),2,2-dichloro-1-(2,2,5-trimethyl-3-oxazolidinyl)-ethanone and2-methoxy-N-[[4-[[(methylamino)carbonyl]amino]phenyl]sulfonyl]-benzamide.

The compounds of Formula 1 can be prepared by general methods known inthe art of synthetic organic chemistry, in combination with the methodsshown below in Schemes 1 through 21 and variations thereof. Thedefinitions of R¹, R², R³, R⁴, R⁵, R⁶, R^(5a), R^(6a), Q¹, Q² and Y inthe compounds of Formulae 1 through 17 below are as defined above in theSummary of the Invention unless otherwise noted. The compounds ofFormulae 1a, 2a, 4a, 6a, 8a, 10a and 13a are various subsets of acompound of Formulae 1, 2, 4, 8, 10 and 13 respectively. The compoundsof Formulae 1b, 2b, 8b, 10b and 13b are various subsets of a compound ofFormulae 1, 2, 8, 10 and 13 respectively. The compounds of Formulae 1c,8c, 10c, and 13c are various subsets of a compound of Formulae 1, 8, 10and 13 respectively. The compounds of Formulae 10d and 10e are varioussubsets of a compound of Formula 10. Substituents for each subsetformula are as defined for its parent formula unless otherwise noted.Substituents of a compound of Formula 1 represented by Q¹ andC(Y)N(Q²)(R⁷), respectively, are predominantly found to be in the transconfiguration. In some instances, the presence of minor amounts of thecis isomer can be detected by NMR.

As shown in Scheme 1 compounds of Formula 1a (i.e. a compound of Formula1 wherein R¹ is H; R² is H; and Y is O) can be prepared by reaction ofesters of Formula 2 with an exess of an amine of Formula 3 by heating attemperatures above 100° C., optionally in the presence of a solvent. Themethod of Scheme 1 is illustrated by Step E in Synthesis Example 1, StepD in Synthesis Examples 2 and 3, and Step A in Synthesis Example 4.

As shown in Scheme 2 a compound of Formula 1b (i.e. a compound ofFormula 1 wherein A is chain containing a carbon or oxygen atom; R⁷ isH; and Y is O) can be prepared by cyclization of a compound of Formula4. Cyclization is carried out using an appropriate nitrogen-containingcompound of Formula 5 such as, but not limited to, aminoacetals,aminoaldehyes, aminoketones and hydrazides, under neutral conditions oracidic conditions. Suitable acids for the reaction include inorganicacids such as hydrochloric acid, hydrobromic acid and sulfuric acid, andorganic acids such as acetic acid and trifluoroacetic acid. A widevariety of co-solvents are suitable for the reaction including, but notlimited to, water, methanol, ethanol and tetrahydrofuran. The reactionis conducted at temperatures ranging from −20° C. to the boiling pointof the solvent, and typically from 0-10° C. The method of Scheme 2 isillustrated by Step D of Synthesis Example 1, Step F of SynthesisExample 3, Step C of Synthesis Example 4, and Step A of SynthesisExample 5.

As shown in Scheme 3 a compound of Formula 1c (i.e. a compound ofFormula 1 wherein R¹ is H; R² is H; Y is O; and A is —NHA²-) can beprepared by cyclization of N-amino lactams of Formula 6 in the presenceof a “coupling partner”. The “coupling partner” for the reaction can bechosen singly or in combination from primary amides, acid chlorides,carbon disulfide, cyanides such as sodium or potassium cyanide orammonia. The cyclization can be carried out optionally in the presenceof an activating agent and typically in the presence of a co-solvent.Suitable activating agents for the reaction include, but are not limitedto, metal chlorides such as zinc chloride and carboxylic acids such asacetic and propionic acid. A wide variety of co-solvents are suitablefor the reaction including, but not limited to, acetic acid, toluene,benzene, xylenes, carbon disulfide, N,N-dimethylformamide andtetrahydrofuran. The reaction is conducted at temperatures ranging from−20° C. to the boiling point of the solvent, and typically from 0-150°C. The method of Scheme 3 is illustrated by Step G of Synthesis Example1.

As shown in Scheme 4 a compound of Formula 1a can also be prepared bycyclization of azido lactams of Formula 8. Cyclization can be carriedout by an organophosphine of Formula 7, typically in the presence of aco-solvent. Suitable organophosphines for the reaction include, but arenot limited to, triphenylphosphine or tri-n-butylphosphine. A widevariety of co-solvents are suitable for the reaction including, but notlimited to, benzene, chlorobenzene, carbon tetrachloride, andtetrahydrofuran. The reaction is conducted at temperatures ranging from−20° C. to the boiling point of the solvent, and typically from 0-100°C. The method of Scheme 4 is illustrated by Step C of Synthesis Example2.

As shown in Scheme 5 a compound of Formula 2a can be prepared bycyclization of a compound of Formula 4a. Cyclization can be carried outusing an appropriate nitrogen-containing compound such as, but notlimited to, aminoacetals, aminoaldehyes, aminoketones and hydrazides,under neutral conditions or acidic conditions. Suitable acids for thereaction include, but are not limited to, inorganic acids such ashydrochloric acid, hydrobromic acid and sulfuric acid, and organic acidssuch as acetic acid and trifluoroacetic acid. A wide variety ofco-solvents are suitable for the reaction including, but not limited to,water, methanol, ethanol and tetrahydrofuran. The reaction is conductedat temperatures ranging from −20° C. to the boiling point of thesolvent, and typically from 0-100° C.

As shown in Scheme 6 a compound of Formula 2b can be prepared bycyclization of azido lactams of Formula 8a. Cyclization can be carriedout by an organophosphine, typically in the presence of a co-solvent.Exemplary organophosphines for the reaction include triphenylphosphineor tri-n-butylphosphine. A wide variety of co-solvents are suitable forthe reaction including, but not limited to, benzene, chlorobenzene,carbon tetrachloride, and tetrahydrofuran. The reaction is conducted attemperatures ranging from −20° C. to the boiling point of the solvent,and typically from 0 to 100° C.

As shown in Scheme 7 a compound of Formula 8b can be prepared bysubstitution of lactams of Formula 9. Substitution is carried out withan inorganic azide or a trialkylsilyl azide, typically in the presenceof a co-solvent. Suitable azides for the reaction include, but are notlimited to, inorganic azides such as sodium azide and trialkylsilylazides such as azidotrimethylsilane. A wide variety of co-solvents aresuitable for the reaction including, but not limited to,N,N-dimethylformamide, N-methyl-2-pyrrolidone, dimethylsulfoxide, andethanol. The reaction is conducted at temperatures ranging from −20° C.to the boiling point of the solvent, and typically from 0-100° C. Themethod of Scheme 7 is illustrated by Step B of Synthesis Example 2.

As shown in Scheme 8 a compound of Formula 8c can be prepared bysubstitution of alcohols of Formula 9 by the Mitsunobu substitutionmethod. It is typically carried out with an azide, a phosphine and anazodicarboxylate, in the presence of a co-solvent. Suitable azides forthe reaction include, but are not limited to, diphenylphosphoryl azideand azidotrimethylsilane. Suitable phosphines for the reaction include,but are not limited to, triphenylphosphine or tri-n-butylphosphine.Suitable phosphines for the reaction include, but are not limited to,diethyl azodicarboxylate and di-tert-butyl azodicarboxylate. A widevariety of co-solvents are suitable for the reaction including, but notlimited to, N,N-dimethylformamide and tetrahydrofuran. The reaction isconducted at temperatures ranging from −20° C. to the boiling point ofthe solvent, and typically from 0-100° C. See Org. Lett. 2008, 10(14),2997-3000 and J. O. C. 1999, 64(16), 6049-6055 for examples of this typeof transformation.

As shown in Scheme 9 a compound of Formula 8b can be prepared byreacting a compound of Formula 10 with a compound of Formula 11.Substitution is carried out optionally in the presence of a base,typically in the presence of a co-solvent. Suitable bases for thereaction include, but are not limited to, hydroxides such as sodium andpotassium hydroxide, carbonates such as sodium and potassium carbonateand nitrogen-containing bases such as triethylamine,N,N-diisopropylamine and 1,8-diazabicyclo[5.4.0]undec-7-ene. A widevariety of co-solvents are suitable for the reaction including, but notlimited to, benzene, toluene, N,N-dimethylformamide,N-methyl-2-pyrrolidone, dimethylsulfoxide, ethanol, methanol,acetonitrile and tetrahydrofuran. The reaction is conducted attemperatures ranging from −20° C. to the boiling point of the solvent,and typically from 0-100° C. A compound of Formula 10 (wherein J is—CR⁵R⁶—) can be prepared in multiple ways as described inPCT/US2014/068073 (WO 2015/084796). A compound of Formula 10 (wherein Jis —CR⁵R⁶—CR^(5a)R^(6a)—) can be prepared in multiple ways as describedin PCT/US2014/38473 (WO 2016/003997).

As shown in Scheme 10 a compound of Formula 6 can be prepared byN-amination of lactams of Formula 10. Amination is carried out with anelectrophilic aminating reagent, optionally in the presence of a baseand typically in the presence of a co-solvent. Suitable electrophilicaminating reagents include, but are not limited to, N-chloroamine,O-diphenylphosphoryl hydroxylamine, O-mesitylsulfonyl hydroxylamine,O-sulfonic acid hydroxylamine, O-mesitoyl hydroxylamine andO-2,4-dinitrophenyl hydroxylamine. Suitable bases for the reactioninclude, but are not limited to, hydroxides such as sodium and potassiumhydroxide, alkoxides such as sodium and potassium ethoxide, carbonatessuch as sodium and potassium carbonate, sodium hydride, metal amidessuch as lithium diisopropylamide and sodium hexamethyldisilazide andneutral nitrogen-containing bases such as triethylamine,N,N-diisopropylamine and 1,8-diazabicyclo[5.4.0]undec-7-ene. A widevariety of co-solvents are suitable for the reaction including, but notlimited to, xylenes, toluene, benzene, diethyl ether,N,N-dimethylformamide and tetrahydrofuran. The reaction is conducted attemperatures ranging from −20° C. to the boiling point of the solvent,and typically from 0-150° C.

Alternatively, N-amination can be achieved by a two-step procedureproceeding through the formation and subsequent reduction of anintermediate N-nitrosolactam of Formula 12. An N-nitrosolactam compoundof Formula 12 can be obtained by carrying out the reaction of a lactamof Formula 10 with an appropriate nitrosylating agent in the presence ofan activator and typically in the presence of a co-solvent. Suitablenitrosylating agents include, but are not limited to, nitrites such assodium and potassium nitrite and nitrogen oxide. Suitable activators forthe reaction include, but are not limited to, acetates such as sodiumand potassium acetate, carboxylic acids such as acetic and propionicacid and Lewis acids such as bismuth(III) trichloride and tin(IV)tetrachloride. A wide variety of co-solvents are suitable for thereaction including, but not limited to, acetic anhydride, carbontetrachloride and methylene chloride. The reaction is conducted attemperatures ranging from −20° C. to the boiling point of the solvent,and typically from 0-100° C. An N-amino compound of Formula 6 can beobtained by carrying out the reaction of a N-nitrosolacatm of Formula 12with an appropriate reducing agent, typically in the presence of aco-solvent. Suitable reducing agents include, but are not limited to,zinc metal. A variety of co-solvents are suitable for the reactionincluding, but not limited to, acetic acid and aqueous hydrochloricacid. The reaction is conducted at temperatures ranging from −20° C. tothe boiling point of the solvent, and typically from −20° C.-100° C. SeeSynthesis 2006, 14, 2371-2375 and Synthetic Communications 2009, 39,604-612 for representative procedures. A compound of Formula 10 (i.e.wherein J is —CR⁵R⁶—) can be prepared in multiple ways as taught inPCT/US2014/068073 (WO 2015/084796). A compound of Formula 10 (wherein Jis —CR⁵R⁶—CR^(5a)R^(6a)—) can be prepared in multiple ways as describedin PCT/US2014/38473 (WO 2016/003997).

Alternatively, as shown in Scheme 11, a compound of Formula 6a can beprepared by reacting a compound of Formula 10a with an aminating reagentsuch as O-(diphenylphosphinyl)hydroxylamine andhydroxylamino-O-sulphonic acid. For procedures, conditions and reagentssee Bioorg. & Med. Chem. Lett. 2009, 19, 5924-5926 and J. O. C. 2002,67, 6236-6239.

As shown in Scheme 12 a compound of Formula 10b can be prepared byhydrolysis of esters of Formula 10a. Hydrolysis is carried out withaqueous base or aqueous acid, typically in the presence of a co-solvent.Suitable bases for the reaction include, but are not limited to,hydroxides such as sodium and potassium hydroxide and carbonates such assodium and potassium carbonate. Suitable acids for the reaction include,but are not limited to, inorganic acids such as hydrochloric acid,hydrobromic acid and sulfuric acid, and organic acids such as aceticacid and trifluoroacetic acid. A wide variety of co-solvents aresuitable for the reaction including, but not limited to, methanol,ethanol and tetrahydrofuran. The reaction is conducted at temperaturesranging from −20° C. to the boiling point of the solvent, and typicallyfrom 0-100° C.

As shown in Scheme 13, a compound of Formula 4 can be obtained byreduction of a compound of Formula 13 and subsequent in situ cyclizationof the resulting intermediate amine. A wide variety of methods forreduction of the aliphatic nitro group in compounds of Formula 13 areknown in the literature. Typical reduction methods include catalytichydrogenation in the presence of palladium on carbon or Raney nickel,iron or zinc metal in acidic medium (see, for example, Berichte derDeutschen Chemischen Gesellschaft 1904, 37, 3520-3525), and lithiumaluminum hydride. Reduction can also be achieved with samarium(II)iodide in the presence of a proton source such as methanol (see forexample, Tet. Lett. 1991, 32 (14), 1699-1702). Alternatively sodiumborohydride in the presence of a nickel catalyst such as nickel(II)acetate or nickel(II) chloride can be used (see for example, Tet. Lett.1985, 26 (52), 6413-6416). The method of Scheme 12 utilizing sodiumborohydride in the presence of nickel(II) chloride hexahydrate isillustrated by Step C of Synthesis Example 1.

As shown in Scheme 14, a compound of Formula 13a (a compound of Formula13 wherein J is —CR⁵R⁶—) can be prepared by reacting diesters of Formula14 with nitroalkanes of Formula 15, typically in the presence of a base.Suitable bases for the reaction include alkali metal lower alkoxidessuch as sodium methoxide in methanol or sodium ethoxide in ethanol. Themethod of Scheme 14 is illustrated by Step B of Synthesis Example 1. Acompound of Formula 14 can readily be prepared by methods known to thoseskilled in the art, e.g., by Knoevenagel condensation of aldehydes andmalonates (see for example G. Jones, Organic Reactions Volume 15, JohnWiley and Sons, 1967).

A compound of Formula 13a (i.e. Formula 13 wherein J is —CR⁵R⁶—) can beprepared by reacting nitroalkenes of Formula 16 with a malonate ofFormula 17 in the presence of a base as shown in Scheme 15. Suitablebases for this reaction include, but are not limited to, alkali metallower alkoxides such as sodium methoxide in methanol or sodium ethoxidein ethanol, or bases such as lithium bis(trimethylsilyl)amide, sodiumbis(trimethylsilyl)amide and lithium diisopropylamide in solvents suchas tetrahydrofuran. Typically, the reaction is carried out in the rangeof from −78° C. to 23° C. See Synthesis 2005, 2239-2245 for conditionsfor effecting this transformation. Conditions for effecting thistransformation in refluxing water in the absence of a catalyst have beenreported in Synthetic Communications 2013, 43, 744-748. Nitroalkenes ofFormula 16 can readily be prepared from aldehydes and nitromethane byknown methods.

Compounds of Formula 13b and 13c can be prepared stereoselectively byreacting nitroalkenes of Formula 16 with malonates of Formula 17 in thepresence of a chiral catalyst and optionally in the presence of asuitable base as shown in Scheme 16. Suitable catalysts include, but arenot limited to Ni(II) with vicinal diamine ligands such as Ni(II)Bis[(R,R)—N,N′-dibenzylcyclohexane-1,2-diamine]dibromide, Ni(II)Bis[(S,S)—N,N-dibenzylcyclohexane-1,2-diamine]dibromide or nickel(II)bromide with chiral 1,1′-bi(tetrahydroisoquinoline) type diamines.Suitable organic bases for this reaction include, but are not limitedto, piperidine, morpholine, triethylamine, 4-methylmorpholine orN,N-diisopropylethylamine. This transformation can be accomplished neator in solvents such as tetrahydrofuran, toluene or dichloromethane.Typically, the reaction is carried out in the range of from 78° C. to80° C. using 0 to 1 equivalent of catalyst and 0 to 1 equivalent of abase. Conditions for effecting this transformation have been reported inJ. Am. Chem. Soc. 2005, 9958-9959 or Eur. J. Org. Chem. 2011, 5441-5446for conditions. Nitroalkenes of Formula 16 can readily be prepared fromaldehydes and nitromethane by methods known to those skilled in the art.

As shown in Scheme 17, mixtures of compounds of Formulae 10b (i.e.Formula 10 wherein Y is O; R¹ is halogen; and R² is H) and 10c (i.e.Formula 10 wherein Y is O; R¹ is H; and R² is halogen) can be preparedby reacting a compound of Formula 10a with a halogen source in asolvent, in the presence or absence of an initiator. Separation of theregioisomers produced in this reaction can be achieved by standardmethods such as chromatography or fractional crystallization. Suitablehalogen sources for this reaction include bromine, chlorine,N-chlorosuccinimide, N-bromosuccinimide and N-iodosuccinimide. Suitableinitiators for this reaction include 2,2′-azobisisobutyronitrile (AIBN)and benzoyl peroxide. Typically, the reaction is carried out in solventssuch as dichloromethane in the range of from 0° C. to the boiling pointof the solvent.

As shown in Scheme 18, compounds of Formula 10d and 10e (i.e. a compoundof Formula 10 wherein R¹ and R² are H; and Y is O (10d) or S (10e),respectively) can be prepared by reacting compounds of Formula 10a withat least two equivalents of a thionation reagent such as Lawesson'sreagent, tetraphosphorus decasulfide or diphosphorus pentasulfide in asolvent such as tetrahydrofuran or toluene. Typically, the reaction iscarried out at temperatures ranging from 0 to 115° C. One skilled in theart recognizes that using less than two equivalents of the thionatingreagent can provide mixtures comprising a products of a compound ofFormulae 10d and 10e (i.e. wherein Y is S or O, respectively) which canbe separated by conventional methods such as chromatography andcrystallization. The method of Scheme 18 is illustrated by Step D ofSynthesis Example 1.

As shown in Scheme 19, compounds of Formula 4 (i.e. Formula 1 wherein R¹and R² are H; and Y is O) can be prepared by alkylation of compounds ofFormula 10a with an appropriate alkylating agent optionally in thepresence of a base. Suitable alkylating agents include, but are notlimited to, trimethyloxonium tetrafluoroborate, triethyloxoniumtetrafluoroborate, iodomethane, iodoethane, bromomethane, and methylp-toluenesulfonate. Suitable bases for the reaction include, but are notlimited to, carbonates such as sodium and potassium carbonate andneutral nitrogen-containing bases such as triethylamine and1,8-diazabicyclo[5.4.0]undec-7-ene. A wide variety of co-solvents aresuitable for the reaction including, but not limited to, acetonitrile,N,N-dimethylformamide and tetrahydrofuran. The reaction is conducted attemperatures ranging from −20° C. to the boiling point of the solvent,and typically from 0-150° C. The method of Scheme 19 is illustrated byStep F of Synthesis Example 1.

It is recognized by one skilled in the art that various functionalgroups can be converted into others to provide different compounds ofFormula 1. For a valuable resource that illustrates the interconversionof functional groups in a simple and straightforward fashion, seeLarock, R. C., Comprehensive Organic Transformations: A Guide toFunctional Group Preparations, 2nd Ed., Wiley-VCH, New York, 1999. Forexample, intermediates for the preparation of compounds of Formula 1 maycontain aromatic nitro groups, which can be reduced to amino groups, andthen be converted via reactions well known in the art such as theSandmeyer reaction, to various halides, providing compounds ofFormula 1. The above reactions can also in many cases be performed inalternate order

It is recognized that some reagents and reaction conditions describedabove for preparing compounds of Formula 1 may not be compatible withcertain functionalities present in the intermediates. In theseinstances, the incorporation of protection/deprotection sequences orfunctional group interconversions into the synthesis will aid inobtaining the desired products. The use and choice of the protectinggroups will be apparent to one skilled in chemical synthesis (see, forexample, Greene, T. W.; Wuts, P. G. M. Protective Groups in OrganicSynthesis, 2nd ed.; Wiley: New York, 1991). One skilled in the art willrecognize that, in some cases, after the introduction of a given reagentas it is depicted in any individual scheme, it may be necessary toperform additional routine synthetic steps not described in detail tocomplete the synthesis of compounds of Formula 1. One skilled in the artwill also recognize that it may be necessary to perform a combination ofthe steps illustrated in the above schemes in an order other than thatimplied by the particular presented to prepare the compounds of Formula1.

One skilled in the art will also recognize that compounds of Formula 1and the intermediates described herein can be subjected to variouselectrophilic, nucleophilic, radical, organometallic, oxidation, andreduction reactions to add substituents or modify existing substituents.

Without further elaboration, it is believed that one skilled in the artusing the preceding description can utilize the present invention to itsfullest extent. The following non-limiting Examples are illustrative ofthe invention. Steps in the following Examples illustrate a procedurefor each step in an overall synthetic transformation, and the startingmaterial for each step may not have necessarily been prepared by aparticular preparative run whose procedure is described in otherExamples or Steps. Percentages are by weight except for chromatographicsolvent mixtures or where otherwise indicated. Parts and percentages forchromatographic solvent mixtures are by volume unless otherwiseindicated. ¹H NMR spectra are reported in ppm downfield fromtetramethylsilane; “s” means singlet, “d” means doublet, “m” meansmultiplet, and “br s” means broad singlet.

Synthesis Example 1 Preparation ofN-(2-fluorophenyl)-6,7-dihydro-6-[3-(trifluoromethyl)phenyl]-5H-pyrrolo[2,1-c]-1,2,4-triazole-7-carboxamide(Compound 2) Step A: Preparation of 1,3-diethyl2-[[3-(trifluoromethyl)phenyl]methylene]propanedioate

A mixture of 3-(trifluoromethyl)benzaldehyde (7.55 g, 43.3 mmol),diethyl malonate (6.6 g, 41.3 mmol), piperidine (0.91 g, 10.7 mmol) andbenzene (50 mL) was refluxed for 17 h with continuous removal of waterusing a Dean-Stark trap. The cooled reaction mixture was concentratedunder reduced pressure, and the residue was chromatographed on silicagel, eluting with 0% to 30% ethyl acetate in hexanes, to afford thetitle compound as a clear, colorless oil (10.9 g).

¹H NMR δ 7.74 (m, 1H), 7.71 (m, 1H), 7.64 (m, 2H), 7.52 (m, 1H), 4.33(m, 4H), 1.35 (m, 3H), 1.29 (m, 3H).

Step B: Preparation of 1,3-diethyl2-[2-nitro-1-[3-(trifluoromethyl)phenyl]ethyl]propanedioate

A mixture of 1,3-diethyl2-[[3-(trifluoromethyl)phenyl]methylene]propanedioate (i.e. the productof Step A, 10.9 g, 34.5 mmol), nitromethane (18.5 mL, 345 mmol) and amethanol solution of sodium methoxide (25 wt %, 0.76 g, 3.45 mmol) inethanol (150 mL) was stirred at 23° C. for 21 h. The reaction mixturewas then concentrated under reduced pressure to afford a thick oil,which was diluted with 25% ethyl acetate in hexanes and filtered througha pad of Celite® diatomaceous earth filter aid to remove insolubleparticulates. The filtrate was concentrated under reduced pressure toafford the title compound as a yellow oil (11.0 g).

¹H NMR δ 7.57 (m, 1H), 7.51 (m, 1H), 7.47 (m, 2H), 4.97 (m, 1H), 4.89(m, 1H), 4.32 (m, 1H), 4.23 (m, 4H), 3.82 (d, J=9.0 Hz, 1H), 1.27 (m,3H), 1.07 (m, 3H).

Step C: Preparation of ethyl2-oxo-4-[3-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxylate

A stirred mixture of 1,3-diethyl2-[2-nitro-1-[3-(trifluoromethyl)phenyl]ethyl]propanedioate (i.e. theproduct of Step B, 11.0 g, 29.0 mmol), nickel(II) chloride hexahydrate(13.8 g, 58.0 mmol) and ethanol (250 mL) was cooled in an ice bath andtreated with sodium borohydride (6.6 g, 174 mmol) in 0.5 g portionsadded over 45 min. The resulting mixture was stirred at 23° C. for 4 h.Saturated ammonium chloride solution (500 mL) was then added, themixture was stirred for 2 h. The aqueous layer was extracted with ethylacetate (3×200 mL). The combined organic extracts were washed withbrine, dried (MgSO₄) and concentrated under reduced pressure. Theresidue was dissolved in ethyl acetate (100 mL) and stirred vigorouslywith saturated ammonium chloride solution (100 mL) for 1 h when all ofthe black particles disappeared. The layers were separated, and theorganic layer was washed with water, dried (MgSO₄) and concentratedunder reduced pressure. The residue was chromatographed on silica gel,eluting with 0% to 100% ethyl acetate in hexanes, to afford the titlecompound as a clear colorless oil.

¹H NMR δ 7.57 (m, 1H), 7.51 (m, 1H), 7.48 (m, 2H), 6.47 (br s, 1H), 4.26(m, 2H), 4.19 (m, 1H), 3.86 (m, 1H), 3.54 (d, J=9.5 Hz, 1H), 3.46 (m,1H), 1.29 (m, 3H).

Step D: Preparation of ethyl2-thioxo-4-[3-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxylate

A mixture of ethyl2-oxo-4-[3-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxylate (i.e. theproduct of Step C, 1.0 g, 3.3 mmol) and Lawesson's reagent (0.67 g, 1.7mmol) in toluene (15 mL) was stirred at reflux for 4 h. The cooledreaction mixture was concentrated under reduced pressure, and theresidue was chromatographed on silica gel, eluting with 0% to 100% ethylacetate in hexanes, to afford the title compound as a yellow oil (0.60g).

¹H NMR δ 8.07 (br s, 1H), 7.57 (m, 1H), 7.49 (m, 2H), 7.44 (m, 1H), 4.28(m, 3H), 4.16 (m, 1H), 3.90 (m, 1H), 3.72 (m, 1H), 1.31 (m, 3H).

Step E: Preparation ofN-(2-fluorophenyl)-2-thioxo-4-[3-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxamide

A mixture of ethyl2-thioxo-4-[3-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxylate (i.e.the product of Step D, 0.55 g, 1.7 mmol) and 2-fluoroaniline (2.0 mL,20.7 mmol) was heated to 120° C. under a nitrogen atmosphere for 71 h.The mixture was chromatographed on silica gel, eluting with 0-40% ethylacetate in hexanes, to afford the title product as an off-white solid(0.49 g).

¹H NMR δ 9.68 (br s, 1H), 8.21 (m, 1H), 7.75 (br s, 1H), 7.57 (m, 2H),7.52 (m, 2H), 7.10 (m, 3H), 4.62 (m, 1H), 4.16 (m, 1H), 3.94 (d, J=6.0Hz, 1H), 3.72 (m, 1H).

Step F: Preparation of N-(2-fluorophenyl)-3,4-dihydro5-methylthio-3-[3-(trifluoromethyl)phenyl]-2H-pyrrole-4-carboxamide

A mixture ofN-(2-fluorophenyl)-2-thioxo-4-[3-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxamide(i.e. the product of Step E, 0.49 g, 1.3 mmol), iodomethane (0.090 mL,1.4 mmol) and potassium carbonate (0.36 g, 2.6 mmol) in acetonitrile (10mL) was stirred at 23° C. for 4 h. The mixture was concentrated underreduced pressure. The residue was taken up in ethyl acetate (20 mL) andwashed with water (2×10 mL). The organic extract was dried (MgSO₄) andconcentrated under reduced pressure to afford the title product as abrown oil (0.39 g).

¹H NMR δ 8.29 (m, 1H), 7.60 (br s, 1H), 7.52 (m, 1H), 7.44 (m, 3H), 7.11(m, 3H), 4.52 (m, 1H), 4.22 (m, 1H), 4.00 (m, 1H), 3.77 (s, 1H), 2.57(m, 3H).

Step G: Preparation ofN-(2-fluorophenyl)-6,7-dihydro-6-[3-(trifluoromethyl)phenyl]-5H-pyrrolo[2,1-c]-1,2,4-triazole-7-carboxamide

A mixture of N-(2-fluorophenyl)-3,4-dihydro5-methylthio-3-[3-(trifluoromethyl)phenyl]-2H-pyrrole-4-carboxamide(i.e. the product of Step F, 0.13 g, 0.33 mmol) and formic hydrazide(0.030 g, 0.50 mmol) in N,N-dimethylacetamide (0.4 mL) was stirred at120° C. for 15 h. The mixture was concentrated under reduced pressure.The residue was chromatographed on silica gel, eluting with 0% to 100%ethyl acetate in hexanes then 0% to 5% methanol in ethyl acetate, toafford the title compound, a compound of the present invention, as abrown oil (0.065 g).

¹H NMR δ 9.17 (br s, 1H), 8.26 (s, 1H), 8.15 (m, 1H), 7.62 (m, 2H), 7.56(m, 3H), 7.09 (m, 3H), 4.93 (m, 1H), 4.61 (m, 1H), 4.36 (d, J=7.4 Hz,1H), 4.14 (m, 1H).

Synthesis Example 2 Preparation ofN-(2-fluorophenyl)-2,3,6,7-tetrahydro-3-oxo-6-[3-(trifluoromethyl)phenyl]-5H-pyrrolo[1,2-a]imidazole-7-carboxamide(Compound 3) Step A: Preparation of ethyl1-(2-chloroacetyl)-2-oxo-4-[3-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxylate

A mixture ethyl2-oxo-4-[3-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxylate (i.e. theproduct of Example 1 Step C, 0.30 g, 1.0 mmol) and chloroacetyl chloride(0.16 mL, 2.0 mmol) in benzene (3 mL) was stirred at 75° C. for 16 h.The cooled reaction mixture was concentrated under reduced pressure toafford the title compound as a dark brown oil (0.37 g).

¹H NMR δ 7.61 (m, 1H), 7.53 (m, 2H), 7.46 (m, 1H), 4.73 (m, 2H), 4.42(m, 1H), 4.27 (m, 2H), 4.10 (m, 1H), 3.82 (d, J=10.7 Hz, 1H), 3.78 (m,1H), 1.30 (m, 3H).

Step B: Preparation of ethyl1-(2-azidoacetyl)-2-oxo-4-[3-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxylate

A mixture of ethyl1-(2-chloroacetyl)-2-oxo-4-[3-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxylate(i.e. the product of Step A, 0.37 g, 1.0 mmol) and sodium azide (0.20 g,3.0 mmol) in N,N-dimethylformamide (3 mL) was stirred at 23° C. for 6 h.The reaction mixture was diluted with ethyl acetate (40 mL). The mixturewas washed successively with water (2×15 mL) and saturated sodiumchloride (15 mL). The organic layer was dried (MgSO₄) and concentratedunder reduced pressure to afford the title compound as a red oil (0.37g).

¹H NMR δ 7.61 (m, 1H), 7.52 (m, 2H), 7.45 (m, 1H), 4.51 (s, 2H), 4.42(m, 1H), 4.27 (m, 2H), 4.10 (m, 1H), 3.80 (d, J=10.9 Hz, 1H), 3.77 (m,1H), 1.29 (m, 3H).

Step C: Preparation of ethyl2,3,6,7-tetrahydro-3-oxo-6-[3-(trifluoromethyl)phenyl]-5H-pyrrolo[1,2-a]imidazole-7-carboxylate

A mixture of ethyl1-(2-azidoacetyl)-2-oxo-4-[3-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxylate(i.e. the product of Step B, 0.37 g, 1.0 mmol) and triphenylphosphine(0.29 g, 1.1 mmol) in benzene (10 mL) was stirred at reflux for 1 h. Thesolution was left to stand at 23° C. for 20 h during which time a solidformed. The mixture was filtered and washed with toluene to afford thetitle compound as a colorless solid (0.20 g). The filtrate wasconcentrated. The residue was dissolved in toluene (4 mL). Magnesiumchloride (0.30 g) was added, and the mixture was stirred at 65° C. for 1h. The cooled reaction mixture was filtered. The filtrate wasconcentrated under reduced pressure to afford an additional quantity ofthe title compound as a colorless solid (0.12 g).

¹H NMR δ 7.49 (m, 2H), 7.43 (m, 2H), 5.72 (br s, 1H), 4.67 (m, 1H), 4.38(m, 2H), 4.15 (m, 1H), 4.02 (m, 2H), 3.59 (m, 1H), 1.08 (br s, 3H).

Step D: Preparation ofN-(2-fluorophenyl)-2,3,6,7-tetrahydro-3-oxo-6-[3-(trifluoromethyl)phenyl]-5H-pyrrolo[1,2-a]imidazole-7-carboxamide

A mixture of ethyl2,3,6,7-tetrahydro-3-oxo-6-[3-(trifluoromethyl)phenyl]-5H-pyrrolo[1,2-a]imidazole-7-carboxylate(i.e. the product of Step C, 0.10 g, 0.29 mmol) and 2-fluoroaniline(0.50 mL, 5.2 mmol) in toluene (3 mL) was heated to 200° C. in amicrowave reactor for 2 h. The cooled reaction mixture waschromatographed on silica gel, eluting with 0-100% ethyl acetate inhexanes, to afford the title product, a compound of the presentinvention, as a yellow oil (0.027 g). The ¹H NMR shows approximately a2:1 mixture of enamine:amidine tautomers.

¹H NMR δ Enamine tautomer 8.20 (m, 1H), 7.58 (m, 4H), 7.07 (m, 3H), 6.37(br s, 1H), 6.27 (br s, 1H), 4.56 (m, 2H), 4.51 (m, 1H), 4.02 (m, 1H),3.59 (m, 1H); Amidine tautomer 9.49 (br s, 1H), 8.20 (m, 1H), 7.58 (m,4H), 7.07 (m, 3H), 4.77 (m, 1H), 4.41 (s, 2H), 4.28 (m, 1H), 4.14 (m,1H), 3.59 (m, 1H).

Synthesis Example 3 Preparation ofN-(2-fluorophenyl)-6,7-dihydro-methyl-6-[4-(trifluoromethyl)phenyl]-5H-pyrrolo[2,1-c]-1,2,4-triazole-7-carboxamide(Compound 24) Step A: Preparation 1,3-dimethyl2-[2-nitro-1-[4-(trifluoromethyl)phenyl]ethyl]-propanedioate

A mixture of 4-(trifluoromethyl)benzaldehyde (25.0 g, 112 mmol),dimethyl malonate (15.6 g, 118 mmol), piperidine (2.39 g, 28.0 mmol) andbenzene (75 mL) was refluxed for 2 h with continuous removal of water(Dean-Stark trap). Acetic acid (3.47 g, 57.7 mmol) was added, and thereaction was heated for another 1.5 h. The cooled reaction mixture waswashed successively with aqueous hydrochloric acid (1 M, 2×40 mL) andsaturated sodium bicarbonate (2×40 mL). The organic layer was dried(Na₂SO₄) and concentrated under reduced pressure to afford a yellow oil(0.37 g). A mixture of the yellow oil, nitromethane (60.0 mL, 1.12 mol)and a methanol solution of sodium methoxide (25 wt %, 2.42 g, 11.2 mmol)in methanol (110 mL) was stirred at 23° C. for 17 h. The reactionmixture was then concentrated under reduced pressure to afford a thickoil. The crude material was filtered through a pad of silica, elutingwith 50% ethyl acetate in hexanes, to afford the title compound as anorange oil (29.0 g).

¹H NMR δ 7.60 (m, 2H), 7.38 (m, 2H), 4.93 (m, 2H), 4.32 (m, 1H), 3.87(d, J=8.8 Hz, 1H), 3.78 (s, 3H), 3.60 (s, 3H).

Step B: Preparation of methyl2-oxo-4-[4-(trifluoromethyl)phenyl]-3-pyrrolidine-carboxylate

A stirred mixture of 1,3-dimethyl2-[2-nitro-1-[4-(trifluoromethyl)phenyl]ethyl]-propanedioate (i.e. theproduct of Step A, 29.0 g, 83.0 mmol), nickel(II) chloride hexahydrate(19.8 g, 83.0 mmol) and methanol (275 mL) was cooled in an ice bath andtreated with sodium borohydride (9.5 g, 250 mmol) in 0.5 g portionsadded over 1 h. The resulting mixture was stirred at 0° C. for 1.5 h andthen at 23° C. for 17 h. Saturated ammonium chloride solution (300 mL)and ethyl acetate (300 mL) was then added, the mixture was stirredvigorously for 2 h. The pale blue mixture was separated. The aqueouslayer was extracted with ethyl acetate (2×100 mL). The combined organicextracts were washed with saturated ammonium chloride solution (100 mL),dried (MgSO₄) and concentrated under reduced pressure. The crude mixturewas triturated with 1-chlorobutane (100 mL) to afford the title compoundas a colorless solid (12.3 g).

¹H NMR δ 7.63 (m, 2H), 7.40 (m, 2H), 6.23 (br s, 1H), 4.21 (m, 1H), 3.86(m, 1H), 3.80 (s, 3H), 3.57 (d, J=9.6 Hz, 1H), 3.45 (m, 1H).

Step C: Preparation of methyl2-thioxo-4-[4-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxylate

A mixture of methyl2-oxo-4-[4-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxylate (i.e. theproduct of Step B, 8.0 g, 27.9 mmol) and Lawesson's reagent (5.63 g,13.9 mmol) in toluene (70 mL) was stirred at reflux for 4.5 h. Thecooled reaction mixture was concentrated under reduced pressure, and theresidue was chromatographed on silica gel, eluting with 0% to 100% ethylacetate in hexanes, to afford a yellow solid consisting of the titlecompound and 20% of an unknown impurity. The mixture was recrystallizedfrom ethyl acetate (100 mL, hot) and hexanes (200 mL, cold) to affordthe title compound as a pale yellow solid (5.0 g).

¹H NMR δ 8.20 (br s, 1H), 7.62 (m, 2H), 7.37 (m, 2H), 4.24 (m, 1H), 4.15(m, 1H), 3.94 (d, J=8.2 Hz, 1H), 3.82 (s, 3H), 3.71 (m, 1H).

Step D: Preparation ofN-(2-fluorophenyl)-2-thioxo-4-[4-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxamide

A mixture of methyl2-thioxo-4-[4-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxylate (i.e.the product of Step C, 1.00 g, 3.3 mmol) and 2-fluoroaniline (2.55 mL,26 mmol) was heated to 130° C. under a nitrogen atmosphere for 22 h. Thereaction was concentrated under reduced pressure to remove the majorityof the excess aniline. The remaining residue was triturated with1-chlorobutane to afford the title compound as a colorless solid (1.18g).

¹H NMR δ 9.67 (br s, 1H), 8.21 (m, 1H), 7.73 (br s, 1H), 7.64 (m, 2H),7.45 (m, 2H), 7.10 (m, 3H), 4.62 (m, 1H), 4.16 (m, 1H), 3.93 (d, J=5.8Hz, 1H), 3.71 (m, 1H).

Step E: Preparation ofN-(2-fluorophenyl)-3,4-dihydro-5-(methylthio)-3-[4-(trifluoromethyl)phenyl]-2H-pyrrole-4-carboxamide

A mixture ofN-(2-fluorophenyl)-2-thioxo-4-[4-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxamide(i.e. the product of Step D, 1.11 g, 2.9 mmol), iodomethane (0.22 mL,3.5 mmol) and potassium carbonate (0.81 g, 5.8 mmol) in acetonitrile (15mL) was stirred at 23° C. for 18 h. The mixture was diluted with water(100 mL) and extracted with ethyl acetate (2×100 mL). The organicextract was dried (MgSO₄) and concentrated under reduced pressure toafford the title product as a brown solid (0.97 g).

¹H NMR δ 8.29 (m, 1H), 7.60 (br s, 1H), 7.52 (m, 1H), 7.44 (m, 3H), 7.11(m, 3H), 4.52 (m, 1H), 4.22 (m, 1H), 4.00 (m, 1H), 3.77 (s, 1H), 2.57(s, 3H).

Step F: Preparation ofN-(2-fluorophenyl)-6,7-dihydro-3-methyl-6-[4-(trifluoromethyl)phenyl]-5H-pyrrolo[2,1-c]-1,2,4-triazole-7-carboxamide

A mixture ofN-(2-fluorophenyl)-3,4-dihydro-5-(methylthio)-3-[4-(trifluoromethyl)phenyl]-2H-pyrrole-4-carboxamide(i.e. the product of Step E, 0.100 g, 0.25 mmol) and acetic hydrazide(0.028 g, 0.38 mmol) in acetic acid (1.2 mL) was stirred at 110° C. for75 min. The mixture was concentrated onto silica gel and chromatographedon silica gel, eluting with 10% to 100% ethyl acetate in hexanes then 0%to 5% methanol in ethyl acetate to afford the title compoundcontaminated with several other impurities. The mixture waschromatographed on C18-silica gel, eluting with 10% to 100% 1:1acetonitrile/methanol in water to afford the title compound, a compoundof the present invention, as a yellow oil (0.021 g).

¹H NMR (d₆-acetone) δ 9.65 (br s, 1H), 8.25 (m, 1H), 7.76 (m, 4H), 7.15(m, 3H), 7.09 (m, 3H), 4.92 (m, 1H), 4.63 (m, 2H), 4.17 (m, 1H), 2.39(s, 3H).

Synthesis Example 4 Preparation ofN-(2,3-difluorophenyl)-3-ethyl-6,7-dihydro-6-[4-(trifluoromethyl)phenyl]-5H-pyrrolo[2,1-c]-1,2,4-triazole-7-carboxamide(Compound 8) Step A: Preparation ofN-(2,3-difluorophenyl)-2-thioxo-4-[4-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxamide

A mixture of methyl2-thioxo-4-[4-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxylate (i.e.the product of Example 3 Step C, 1.00 g, 3.3 mmol) and2,3-difluoroaniline (3.4 g, 26 mmol) was heated to 130° C. under anitrogen atmosphere for 22 h. The reaction was concentrated underreduced pressure to remove the majority of the excess aniline. Theremaining residue was triturated with 1-chlorobutane to afford the titlecompound as a colorless solid (1.13 g).

¹H NMR δ 9.84 (br s, 1H), 7.97 (m, 1H), 7.75 (br s, 1H), 7.64 (m, 2H),7.45 (m, 2H), 7.04 (m, 1H), 6.92 (m, 1H), 4.60 (m, 1H), 4.15 (m, 1H),3.94 (d, J=6.3 Hz, 1H), 3.72 (m, 1H).

Step B: Preparation ofN-(2,3-difluorophenyl)-3,4-dihydro-5-(methylthio)-3-[4-(trifluoromethyl)phenyl]-2H-pyrrole-4-carboxamide

A mixture ofN-(2,3-difluorophenyl)-2-thioxo-4-[4-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxamide(i.e. the product of Step A, 1.16 g, 2.9 mmol), iodomethane (0.22 mL,3.5 mmol) and potassium carbonate (0.81 g, 5.8 mmol) in acetonitrile (15mL) was stirred at 23° C. for 18 h. The mixture was diluted with water(100 mL) and extracted with ethyl acetate (2×100 mL). The organicextract was dried (MgSO₄) and concentrated under reduced pressure toafford the title product as a brown solid (1.10 g).

¹H NMR δ 8.06 (m, 1H), 7.60 (m, 3H), 7.33 (m, 2H), 7.07 (m, 1H), 6.94(m, 1H), 4.51 (m, 1H), 4.22 (m, 1H), 4.01 (m, 1H), 3.77 (s, 1H), 2.58(s, 3H).

Step C: Preparation ofN-(2,3-difluorophenyl)-3-ethyl-6,7-dihydro-6-[4-(trifluoromethyl)phenyl]-5H-pyrrolo[2,1-c]-1,2,4-triazole-7-carboxamide

A mixture ofN-(2,3-difluorophenyl)-3,4-dihydro-5-(methylthio)-3-[4-(trifluoromethyl)phenyl]-2H-pyrrole-4-carboxamide(i.e. the product of Step B, 0.200 g, 0.48 mmol) and hydrazine hydrate(0.036 mL, 0.72 mmol) in propionic acid (2.4 mL) was stirred at 110° C.for 16.5 h. The mixture was concentrated onto Celite® diatomaceous earthfilter aid and chromatographed on C18-silica gel, eluting with 10% to100% 1:1 acetonitrile/methanol in water to afford the title compound, acompound of the present invention, as a brown solid (0.037 g).

¹H NMR δ 10.19 (br s, 1H), 7.82 (m, 1H), 7.64 (m, 2H), 7.47 (m, 2H),6.92 (m, 1H), 6.83 (m, 1H), 4.99 (m, 1H), 4.50 (m, 2H), 3.98 (m, 1H),2.81 (m, 2H), 1.37 (m, 3H).

Synthesis Example 5 Preparation ofN-(2,3-difluorophenyl)-6,7-dihydro-3-(trifluoromethyl)-6-[4-(trifluoromethyl)phenyl]-5H-pyrrolo[2,1-c]-1,2,4-triazole-7-carboxamide(Compound 22) Step A: Preparation ofN-(2,3-difluorophenyl)-6,7-dihydro-3-(trifluoromethyl)-6-[4-(trifluoromethyl)phenyl]-5H-pyrrolo[2,1-c]-1,2,4-triazole-7-carboxamide

A mixture ofN-(2,3-difluorophenyl)-3,4-dihydro-5-(methylthio)-3-[4-(trifluoromethyl)phenyl]-2H-pyrrole-4-carboxamide(i.e. the product of Example 4 Step B, 0.220 g, 0.53 mmol),trifluoroacetic hydrazide (0.076 g, 0.58 mmol) and pivalic acid (2.7 g)was stirred at 130° C. for 90 min. The cooled mixture was diluted withethyl acetate (100 mL) and washed successively with saturated sodiumbicarbonate (50 mL), water (50 mL) and saturated sodium chloride (50mL). The organic layer was dried (MgSO₄), concentrated onto Celite®diatomaceous earth filter aid and chromatographed on C18-silica gel,eluting with 10% to 100% 1:1 acetonitrile/methanol in water to affordthe title compound contaminated with some impurities. The mixture wastriturated with 1-chlorobutane to afford the title compound, a compoundof the present invention, as a colorless solid (0.029 g).

¹H NMR δ 9.25 (br s, 1H), 7.89 (m, 1H), 7.70 (m, 2H), 7.51 (m, 2H), 7.03(m, 1H), 6.92 (m, 1H), 5.04 (m, 1H), 4.71 (m, 1H), 4.46 (d, J=7.6 Hz,1H), 4.24 (m, 1H).

By the procedures described herein together with methods known in theart, the following compounds of Tables 1 to 140 can be prepared. Thefollowing abbreviations are used in the Tables which follow: i-Pr meansisopropyl, Bu means butyl, Ph means phenyl, OMe means methoxy, OEt meansethoxy, SMe means methylthio, \S(O)Me means methylsulfinyl, and S(O)₂Memeans methyl sulfonyl.

TABLE 1

J is —CH₂—; Q² is Ph(2-F); and Q¹ is Q¹ Q¹ Q¹ Ph(3-Cl) Ph(4-OCF₃)2-Pyridinyl(3-CF₃) Ph(3-F) Ph(4-OCF₂H) 2-Pyridinyl(3-Me) Ph(3-Br)Ph(4-OMe) 3-Pyridinyl Ph(3-Me) Ph(4-CH₂CF₃) 3-Pyridinyl(6-F) Ph(3-Et)Ph(4-O—i-Pr) 3-Pyridinyl(6-CF₃) Ph(3-CF₃) Ph(4-OCF₂CF₂H)3-Pyridinyl(6-Me) Ph(3-CH₂CF₃) Ph(2,3-di-F) 3-Pyridinyl(5-F) Ph(3-OCF₃)Ph(2,4-di-F) 3-Pyridinyl(5-CF₃) Ph(3-OCF₂H) Ph(2,5-di-F)3-Pyridinyl(5-Me) Ph(3-O—i-Pr) Ph(2,6-di-F) 3-Pyridinyl(4-F) Ph(3-OMe)Ph(3,4-di-F) 3-Pyridinyl(4-CF₃) Ph(3-OCF₂CF₂H) Ph(3,5-di-F)3-Pyridinyl(4-Me) Ph(2-Cl) Ph(3-Me,4-F) 3-Pyridinyl(2-F) Ph(2-F)Ph(3-F,4-Me) 3-Pyridinyl(2-CF₃) Ph(2-Br) Ph(3-CF₃,4-F) 3-Pyridinyl(2-Me)Ph(2-Me) Ph(3-F,4-CF₃) 4-Pyridinyl Ph(2-CF₃) Ph(2,3,4-tri-F)4-Pyridinyl(6-F) Ph(2-OCF₃) Ph(3,4,5-tri-F) 4-Pyridinyl(6-CF₃)Ph(2-OCF₂H) 2-Pyridinyl 4-Pyridinyl(6-Me) Ph(2-OMe) 2-Pyridinyl(6-F)4-Pyridinyl(5-F) Ph(2-OCF₂CF₂H) 2-Pyridinyl(6-CF₃) 4-Pyridinyl(5-CF₃)Ph(2-CH₂CF₃) 2-Pyridinyl(6-Me) 4-Pyridinyl(5-Me) Ph(2-O—i-Pr)2-Pyridinyl(5-F) 4-Pyridinyl(3-F) Ph(4-Cl) 2-Pyridinyl(5-CF₃)4-Pyridinyl(3-CF₃) Ph(4-F) 2-Pyridinyl(5-Me) 4-Pyridinyl(3-Me) Ph(4-Br)2-Pyridinyl(4-F) 4-Pyridinyl(2-F) Ph(4-Me) 2-Pyridinyl(4-CF₃)4-Pyridinyl(2-CF₃) Ph(4-Et) 2-Pyridinyl(4-Me) 4-Pyridinyl(2-Me)Ph(4-CF₃) 2-Pyridinyl(3-F) 2-Thienyl 2-Thienyl(4-CF₃) Oxazol-2-yl7-Quinolinyl 2-Thienyl(5-CF₃) Oxazol-2-yl(5-CF₃) Indazol-1-yl 3-ThienylOxazol-5-yl Benzimidazol-1-yl 3-Thienyl(4-CF₃) Oxazol-5-yl(2-CF₃)Indol-1-yl 3-Thienyl(5-CF₃) Isothiazol-5-yl Pyrrolo[2,3-c]pyridin-1-yl2-Furyl Isothiazol-5-yl(3-CF₃) Ph(3-OCH₂—c-Pr) 2-Furyl(4-CF₃)Isothiazol-3-yl Ph(2-OCH₂—c-Pr) 2-Furyl(5-CF₃) Isothiazol-3-yl(5-CF₃)Ph(4-OCH₂CH₂CH₂CH₂-c-hex) 3-Furyl Isoxazol-5-yl Ph(CH₂—c-Pr)3-Furyl(4-CF₃) Isoxazol-5-yl(3-CF₃) Ph(4-CH₂CH₂CH₂CH₂-c-hex)3-Furyl(5-CF₃) Isoxazol-3-yl Ph(3-OCH₂CF₂) 1H-Pyrazol-1-ylIsoxazol-3-yl(5-CF₃) Ph(2-(3,3-dichloroallyloxy)) 4-CF₃-1H-Pyrazol-1-yl1H-1,2,3,4-Tetrazol-1-yl Ph(2-methoxyethoxy) 1H-Imidazol-1-yl5-Me-1H-1,2,3,4-Tetrazol-1-yl Ph(3-propoxypropoxy)4-CF₃-1H-Imidazol-1-yl 1-Me-1H-1,2,3,4-Tetrazol-5-yl Ph(2-CH₂CH₂SCH₃)2-CF₃-1H-Imidazol-1-yl 1H-1,2,4-Triazol-1-yl Ph(2-CH₂CH₂SOCH₃)1-Me-1H-Imidazol-2-yl 1,3,4-Oxadiazol-2-yl Ph(2-CH₂CH₂SO₂CH₃)1-Me-1H-Imidazol-4-yl 1,3,4-Thiadiazol-2-yl Ph(3-SMe)3-Me-1H-Imidazol-4-yl 1,2,4-Oxadiazol-3-yl Ph(3-SCF₃)1-Me-1H-Pyrazol-4-yl 1,2,4-Thiadiazol-3-yl Ph(3-S—c-Pr)1-Me-1H-1,2,3-Triazol-4-yl Tetrahydropyran-2-yl Ph(3-SOMe)2-Me-1H-1,2,3-Triazol-4-yl Tetrahydropyran-3-yl Ph(3-SOCF₃)4-Me-1H-1,2,3-Triazol-2-yl Tetrahydrofuran-2-yl Ph(3-SO—c-Pr)4-Me-1H-1,2,3-Triazol-1-yl Tetrahydrofuran-3-yl Ph(3-SO₂Me) Pyrazin-2-yl1,3-Dioxolan-4-yl Ph(3-SO₂CF₃) Pyrazin-2-yl(5-CF₃)2,2-di-Fluoro-1,3-Dioxolan-4-yl Ph(3-SO₂—c-Pr) Pyrimidin-2-yl1,3-Dithiolan-4-yl Ph(3-propargyl) Pyrimidin-2-yl(5-CF₃)1,4-Dioxolan-2-yl Ph(3-(2-Butynyl)) Pyrimidin-5-yl 1,4-Dithiolan-2-ylPh(2-CH₂CH₂OCH₂CH₃) Pyrimidin-5-yl(2-CF₃) 1-naphthyl Ph(2-C(═O)CH₃)1,3,5-Triazin-2-yl 2-naphthyl Ph(2-OC(═O)CH₃) Thiazol-2-ylBenzofuran-2-yl Ph(3-OC(═O)CH₃) Thiazol-2-yl(5-CF₃) Benzothiophen-2-ylPh(2-OC(═O)CF₃) Thiazol-5-yl 1,3-Benzoxazol-2-yl Ph(3-OC(O)CF₃)Thiazol-5-yl(2-CF₃) 1,3-Benzothiazol-2-yl

Table 2 is constructed in the same manner except that the Row Heading “Jis —CH₂—; Q² is Ph(2-F); and Q¹ is” is replaced with the Row Headinglisted for Table 2 below (i.e. “J is —CH₂—; Q² is Ph(2,3-di-F); and Q¹is”). Therefore the first entry in Table 2 is a compound of Formula 1wherein J is —CH₂—; Q² is Ph(2,3-di-F); and Q¹ is Ph(3-Cl) (i.e.3-chlorophenyl). Tables 3 through 20 are constructed similarly.

TABLE 21 Table Row Heading 2 J is —CH₂—; Q² is Ph(2,3-di-F); and Q¹ is 3J is —CH₂—; Q² is Ph(2,4-di-F); and Q¹ is 4 J is —CH₂—; Q² isPh(2,3,4-tri-F); and Q¹ is 5 J is —CH₂—; Q² is Ph(2-CF₃); and Q¹ is 6 Jis —CH₂—; Q² is Ph(2-Me); and Q¹ is 7 J is —CH₂—; Q² is Ph(2-NO₂); andQ¹ is 8 J is —CH₂—; Q² is Ph(2-Cl); and Q¹ is 9 J is —CH₂—; Q² isPh(2-SO₂Me); and Q¹ is 10 J is —CH₂—; Q² is Ph(2-F,3-Cl); and Q¹ is 11 Jis —CH₂CH₂—; Q² is Ph(2-F); and Q¹ is 12 J is —CH₂CH₂—; Q² isPh(2,3-di-F); and Q¹ is 13 J is —CH₂CH₂—; Q² is Ph(2,4-di-F); and Q¹ is14 J is —CH₂CH₂—; Q² is Ph(2,3,4-tri-F); and Q¹ is 15 J is —CH₂CH₂—; Q²is Ph(2-CF₃); and Q¹ is 16 J is —CH₂CH₂—; Q² is Ph(2-Me); and Q¹ is 17 Jis —CH₂CH₂—; Q² is Ph(2-NO₂); and Q¹ is 18 J is —CH₂CH₂—; Q² isPh(2-Cl); and Q¹ is 19 J is —CH₂CH₂—; Q² is Ph(2-SO₂Me); and Q¹ is 20 Jis —CH₂CH₂—; Q² is Ph(2-F,3-Cl); and Q¹ is

Table 21 is constructed the same way as Table 1 above, except thestructure is replaced with the following:

Tables 22 Through 40

This disclosure also includes Tables 22 through 40, each Table isconstructed in the same fashion as Tables 2 through 20 above, exceptthat the structure is replaced with the structure in Table 21 above.

Table 41

Table 41 is constructed the same way as Table 1 above, except thestructure is replaced with the following:

Tables 42 Through 60

This disclosure also includes Tables 42 through 60, each Table isconstructed in the same fashion as Tables 2 through 20 above, exceptthat the structure is replaced with the structure in Table 41 above.

Table 61

Table 61 is constructed the same way as Table 1 above, except thestructure is replaced with the following:

Tables 62 Through 80

This disclosure also includes Tables 62 through 80, each Table isconstructed in the same fashion as Tables 2 through 20 above, exceptthat the structure is replaced with the structure in Table 61 above.

Table 81

Table 81 is constructed the same way as Table 1 above, except thestructure is replaced with the following:

Tables 82 Through 100

This disclosure also includes Tables 82 through 100, each Table isconstructed in the same fashion as Tables 2 through 20 above, exceptthat the structure is replaced with the structure in Table 81 above.

Table 101

Table 101 is constructed the same way as Table 1 above, except thestructure is replaced with the following:

Tables 102 Through 120

This disclosure also includes Tables 102 through 120, each Table isconstructed in the same fashion as Tables 2 through 20 above, exceptthat the structure is replaced with the structure in Table 101 above.

Table 121

Table 121 is constructed the same way as Table 1 above, except thestructure is replaced with the following:

Tables 122 Through 140

This disclosure also includes Tables 122 through 140, each Table isconstructed in the same fashion as Tables 2 through 20 above, exceptthat the structure is replaced with the structure in Table 121 above.

A compound of this invention will generally be used as a herbicidalactive ingredient in a composition, i.e. formulation, with at least oneadditional component selected from the group consisting of surfactants,solid diluents and liquid diluents, which serves as a carrier. Theformulation or composition ingredients are selected to be consistentwith the physical properties of the active ingredient, mode ofapplication and environmental factors such as soil type, moisture andtemperature.

Useful formulations include both liquid and solid compositions. Liquidcompositions include solutions (including emulsifiable concentrates),suspensions, emulsions (including microemulsions, oil-in-wateremulsions, flowable concentrates and/or suspoemulsions) and the like,which optionally can be thickened into gels. The general types ofaqueous liquid compositions are soluble concentrate, suspensionconcentrate, capsule suspension, concentrated emulsion, microemulsion,oil-in-water emulsion, flowable concentrate and suspo-emulsion. Thegeneral types of nonaqueous liquid compositions are emulsifiableconcentrate, microemulsifiable concentrate, dispersible concentrate andoil dispersion.

The general types of solid compositions are dusts, powders, granules,pellets, prills, pastilles, tablets, filled films (including seedcoatings) and the like, which can be water-dispersible (“wettable”) orwater-soluble. Films and coatings formed from film-forming solutions orflowable suspensions are particularly useful for seed treatment. Activeingredient can be (micro)encapsulated and further formed into asuspension or solid formulation; alternatively the entire formulation ofactive ingredient can be encapsulated (or “overcoated”). Encapsulationcan control or delay release of the active ingredient. An emulsifiablegranule combines the advantages of both an emulsifiable concentrateformulation and a dry granular formulation. High-strength compositionsare primarily used as intermediates for further formulation.

Sprayable formulations are typically extended in a suitable mediumbefore spraying. Such liquid and solid formulations are formulated to bereadily diluted in the spray medium, usually water, but occasionallyanother suitable medium like an aromatic or paraffinic hydrocarbon orvegetable oil. Spray volumes can range from about from about one toseveral thousand liters per hectare, but more typically are in the rangefrom about ten to several hundred liters per hectare. Sprayableformulations can be tank mixed with water or another suitable medium forfoliar treatment by aerial or ground application, or for application tothe growing medium of the plant. Liquid and dry formulations can bemetered directly into drip irrigation systems or metered into the furrowduring planting.

The formulations will typically contain effective amounts of activeingredient, diluent and surfactant within the following approximateranges which add up to 100 percent by weight.

Weight Percent Active Ingredient Diluent Surfactant Water Dispersibleand Water- 0.001-90 0-99.999 0-15 soluble Granules, Tablets and PowdersOil Dispersions, Suspensions,    1-50 40-99    0-50 Emulsions, Solutions(including Emulsifiable Concentrates) Dusts    1-25 70-99    0-5 Granules and Pellets 0.001-99 5-99.999 0-15 High Strength Compositions  90-99 0-10    0-2 

Solid diluents include, for example, clays such as bentonite,montmorillonite, attapulgite and kaolin, gypsum, cellulose, titaniumdioxide, zinc oxide, starch, dextrin, sugars (e.g., lactose, sucrose),silica, talc, mica, diatomaceous earth, urea, calcium carbonate, sodiumcarbonate and bicarbonate, and sodium sulfate. Typical solid diluentsare described in Watkins et al., Handbook of Insecticide Dust Diluentsand Carriers, 2nd Ed., Dorland Books, Caldwell, N.J.

Liquid diluents include, for example, water, N,N-dimethylalkanamides(e.g., N,N-dimethylformamide), limonene, dimethyl sulfoxide,N-alkylpyrrolidones (e.g., N-methylpyrrolidinone), alkyl phosphates(e.g., triethyl phosphate), ethylene glycol, triethylene glycol,propylene glycol, dipropylene glycol, polypropylene glycol, propylenecarbonate, butylene carbonate, paraffins (e.g., white mineral oils,normal paraffins, isoparaffins), alkylbenzenes, alkylnaphthalenes,glycerine, glycerol triacetate, sorbitol, aromatic hydrocarbons,dearomatized aliphatics, alkylbenzenes, alkylnaphthalenes, ketones suchas cyclohexanone, 2-heptanone, isophorone and4-hydroxy-4-methyl-2-pentanone, acetates such as isoamyl acetate, hexylacetate, heptyl acetate, octyl acetate, nonyl acetate, tridecyl acetateand isobornyl acetate, other esters such as alkylated lactate esters,dibasic esters, alkyl and aryl benzoates and γ-butyrolactone, andalcohols, which can be linear, branched, saturated or unsaturated, suchas methanol, ethanol, n-propanol, isopropyl alcohol, n-butanol, isobutylalcohol, n-hexanol, 2-ethylhexanol, n-octanol, decanol, isodecylalcohol, isooctadecanol, cetyl alcohol, lauryl alcohol, tridecylalcohol, oleyl alcohol, cyclohexanol, tetrahydrofurfuryl alcohol,diacetone alcohol, cresol and benzyl alcohol. Liquid diluents alsoinclude glycerol esters of saturated and unsaturated fatty acids(typically C₆-C₂₂), such as plant seed and fruit oils (e.g., oils ofolive, castor, linseed, sesame, corn (maize), peanut, sunflower,grapeseed, safflower, cottonseed, soybean, rapeseed, coconut and palmkernel), animal-sourced fats (e.g., beef tallow, pork tallow, lard, codliver oil, fish oil), and mixtures thereof. Liquid diluents also includealkylated fatty acids (e.g., methylated, ethylated, butylated) whereinthe fatty acids may be obtained by hydrolysis of glycerol esters fromplant and animal sources, and can be purified by distillation. Typicalliquid diluents are described in Marsden, Solvents Guide, 2nd Ed.,Interscience, New York, 1950.

The solid and liquid compositions of the present invention often includeone or more surfactants. When added to a liquid, surfactants (also knownas “surface-active agents”) generally modify, most often reduce, thesurface tension of the liquid. Depending on the nature of thehydrophilic and lipophilic groups in a surfactant molecule, surfactantscan be useful as wetting agents, dispersants, emulsifiers or defoamingagents.

Surfactants can be classified as nonionic, anionic or cationic. Nonionicsurfactants useful for the present compositions include, but are notlimited to: alcohol alkoxylates such as alcohol alkoxylates based onnatural and synthetic alcohols (which may be branched or linear) andprepared from the alcohols and ethylene oxide, propylene oxide, butyleneoxide or mixtures thereof; amine ethoxylates, alkanolamides andethoxylated alkanolamides; alkoxylated triglycerides such as ethoxylatedsoybean, castor and rapeseed oils; alkylphenol alkoxylates such asoctylphenol ethoxylates, nonylphenol ethoxylates, dinonyl phenolethoxylates and dodecyl phenol ethoxylates (prepared from the phenolsand ethylene oxide, propylene oxide, butylene oxide or mixturesthereof); block polymers prepared from ethylene oxide or propylene oxideand reverse block polymers where the terminal blocks are prepared frompropylene oxide; ethoxylated fatty acids; ethoxylated fatty esters andoils; ethoxylated methyl esters; ethoxylated tristyrylphenol (includingthose prepared from ethylene oxide, propylene oxide, butylene oxide ormixtures thereof); fatty acid esters, glycerol esters, lanolin-basedderivatives, polyethoxylate esters such as polyethoxylated sorbitanfatty acid esters, polyethoxylated sorbitol fatty acid esters andpolyethoxylated glycerol fatty acid esters; other sorbitan derivativessuch as sorbitan esters; polymeric surfactants such as randomcopolymers, block copolymers, alkyd peg (polyethylene glycol) resins,graft or comb polymers and star polymers; polyethylene glycols (pegs);polyethylene glycol fatty acid esters; silicone-based surfactants; andsugar-derivatives such as sucrose esters, alkyl polyglycosides and alkylpolysaccharides.

Useful anionic surfactants include, but are not limited to: alkylarylsulfonic acids and their salts; carboxylated alcohol or alkylphenolethoxylates; diphenyl sulfonate derivatives; lignin and ligninderivatives such as lignosulfonates; maleic or succinic acids or theiranhydrides; olefin sulfonates; phosphate esters such as phosphate estersof alcohol alkoxylates, phosphate esters of alkylphenol alkoxylates andphosphate esters of styryl phenol ethoxylates; protein-basedsurfactants; sarcosine derivatives; styryl phenol ether sulfate;sulfates and sulfonates of oils and fatty acids; sulfates and sulfonatesof ethoxylated alkylphenols; sulfates of alcohols; sulfates ofethoxylated alcohols; sulfonates of amines and amides such asN,N-alkyltaurates; sulfonates of benzene, cumene, toluene, xylene, anddodecyl and tridecylbenzenes; sulfonates of condensed naphthalenes;sulfonates of naphthalene and alkyl naphthalene; sulfonates offractionated petroleum; sulfosuccinamates; and sulfosuccinates and theirderivatives such as dialkyl sulfosuccinate salts.

Useful cationic surfactants include, but are not limited to: amides andethoxylated amides; amines such as N-alkyl propanediamines,tripropylenetriamines and dipropylenetetramines, and ethoxylated amines,ethoxylated diamines and propoxylated amines (prepared from the aminesand ethylene oxide, propylene oxide, butylene oxide or mixturesthereof); amine salts such as amine acetates and diamine salts;quaternary ammonium salts such as quaternary salts, ethoxylatedquaternary salts and diquaternary salts; and amine oxides such asalkyldimethylamine oxides and bis-(2-hydroxyethyl)-alkylamine oxides.

Also useful for the present compositions are mixtures of nonionic andanionic surfactants or mixtures of nonionic and cationic surfactants.Nonionic, anionic and cationic surfactants and their recommended usesare disclosed in a variety of published references includingMcCutcheon's Emulsifiers and Detergents, annual American andInternational Editions published by McCutcheon's Division, TheManufacturing Confectioner Publishing Co.; Sisely and Wood, Encyclopediaof Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964; andA. S. Davidson and B. Milwidsky, Synthetic Detergents, Seventh Edition,John Wiley and Sons, New York, 1987.

Compositions of this invention may also contain formulation auxiliariesand additives, known to those skilled in the art as formulation aids(some of which may be considered to also function as solid diluents,liquid diluents or surfactants). Such formulation auxiliaries andadditives may control: pH (buffers), foaming during processing(antifoams such polyorganosiloxanes), sedimentation of activeingredients (suspending agents), viscosity (thixotropic thickeners),in-container microbial growth (antimicrobials), product freezing(antifreezes), color (dyes/pigment dispersions), wash-off (film formersor stickers), evaporation (evaporation retardants), and otherformulation attributes. Film formers include, for example, polyvinylacetates, polyvinyl acetate copolymers, polyvinylpyrrolidone-vinylacetate copolymer, polyvinyl alcohols, polyvinyl alcohol copolymers andwaxes. Examples of formulation auxiliaries and additives include thoselisted in McCutcheon's Volume 2: Functional Materials, annualInternational and North American editions published by McCutcheon'sDivision, The Manufacturing Confectioner Publishing Co.; and PCTPublication WO 03/024222.

The compound of Formula 1 and any other active ingredients are typicallyincorporated into the present compositions by dissolving the activeingredient in a solvent or by grinding in a liquid or dry diluent.Solutions, including emulsifiable concentrates, can be prepared bysimply mixing the ingredients. If the solvent of a liquid compositionintended for use as an emulsifiable concentrate is water-immiscible, anemulsifier is typically added to emulsify the active-containing solventupon dilution with water. Active ingredient slurries, with particlediameters of up to 2,000 μm can be wet milled using media mills toobtain particles with average diameters below 3 μm. Aqueous slurries canbe made into finished suspension concentrates (see, for example, U.S.Pat. No. 3,060,084) or further processed by spray drying to formwater-dispersible granules. Dry formulations usually require dry millingprocesses, which produce average particle diameters in the 2 to 10 μmrange. Dusts and powders can be prepared by blending and usuallygrinding (such as with a hammer mill or fluid-energy mill). Granules andpellets can be prepared by spraying the active material upon preformedgranular carriers or by agglomeration techniques. See Browning,“Agglomeration”, Chemical Engineering, Dec. 4, 1967, pp 147-48, Perry'sChemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963,pages 8-57 and following, and WO 91/13546. Pellets can be prepared asdescribed in U.S. Pat. No. 4,172,714. Water-dispersible andwater-soluble granules can be prepared as taught in U.S. Pat. Nos.4,144,050, 3,920,442 and DE 3,246,493. Tablets can be prepared as taughtin U.S. Pat. Nos. 5,180,587, 5,232,701 and 5,208,030. Films can beprepared as taught in GB 2,095,558 and U.S. Pat. No. 3,299,566.

For further information regarding the art of formulation, see T. S.Woods, “The Formulator's Toolbox—Product Forms for Modern Agriculture”in Pesticide Chemistry and Bioscience, The Food—Environment Challenge,T. Brooks and T. R. Roberts, Eds., Proceedings of the 9th InternationalCongress on Pesticide Chemistry, The Royal Society of Chemistry,Cambridge, 1999, pp. 120-133. See also U.S. Pat. No. 3,235,361, Col. 6,line 16 through Col. 7, line 19 and Examples 10-41; U.S. Pat. No.3,309,192, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12,15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182;U.S. Pat. No. 2,891,855, Col. 3, line 66 through Col. 5, line 17 andExamples 1-4; Klingman, Weed Control as a Science, John Wiley and Sons,Inc., New York, 1961, pp 81-96; Hance et al., Weed Control Handbook, 8thEd., Blackwell Scientific Publications, Oxford, 1989; and Developmentsin formulation technology, NB Publications, Richmond, UK, 2000.

In the following Examples, all percentages are by weight and allformulations are prepared in conventional ways. Compound numbers referto compounds in Index Table A. Without further elaboration, it isbelieved that one skilled in the art using the preceding description canutilize the present invention to its fullest extent. The followingExamples are, therefore, to be construed as merely illustrative, and notlimiting of the disclosure in any way whatsoever. Percentages are byweight except where otherwise indicated.

Example A

High Strength Concentrate

Compound 1 98.5% silica aerogel 0.5% synthetic amorphous fine silica1.0%

Example B

Wettable Powder

Compound 1 65.0% dodecylphenol polyethylene glycol ether 2.0% sodiumligninsulfonate 4.0% sodium silicoaluminate 6.0% montmorillonite(calcined) 23.0%

Example C

Granule

Compound 1 10.0% attapulgite granules (low volatile matter, 0.71/0.30mm; 90.0% U.S.S. No. 25-50 sieves)

Example D

Extruded Pellet

Compound 1 25.0% anhydrous sodium sulfate 10.0% crude calciumligninsulfonate 5.0% sodium alkylnaphthalenesulfonate 1.0%calcium/magnesium bentonite 59.0%

Example E

Emulsifiable Concentrate

Compound 1 10.0% polyoxyethylene sorbitol hexoleate 20.0% C₆-C₁₀ fattyacid methyl ester 70.0%

Example F

Microemulsion

Compound 1 5.0% polyvinylpyrrolidone-vinyl acetate copolymer 30.0%alkylpolyglycoside 30.0% glyceryl monooleate 15.0% water 20.0%

Example G

Suspension Concentrate

Compound 1  35% butyl polyoxyethylene/polypropylene block copolymer 4.0%stearic acid/polyethylene glycol copolymer 1.0% styrene acrylic polymer1.0% xanthan gum 0.1% propylene glycol 5.0% silicone based defoamer 0.1%1,2-benzisothiazolin-3-one 0.1% water 53.7% 

Example H

Emulsion in Water

Compound 1 10.0% butyl polyoxyethylene/polypropylene block copolymer4.0% stearic acid/polyethylene glycol copolymer 1.0% styrene acrylicpolymer 1.0% xanthan gum 0.1% propylene glycol 5.0% silicone baseddefoamer 0.1% 1,2-benzisothiazolin-3-one 0.1% aromatic petroleum basedhydrocarbon 20.0 water 58.7%

Example I

Oil Dispersion

Compound 1 25% polyoxyethylene sorbitol hexaoleate 15% organicallymodified bentonite clay 2.5%  fatty acid methyl ester 57.5% 

The present disclosure also includes Formulation Examples A through Iabove except “Compound is 1” in each of the above Examples A through Iis replaced with “Compound 2”, “Compound 3” “Compound 4” “Compound 5”,“Compound 6”, “Compound 7”, “Compound 8”, “Compound 9”, “Compound 10”,“Compound 11”, “Compound 12”, “Compound 13”, “Compound 14”, “Compound15”, “Compound 16”, “Compound 17”, “Compound 18”, “Compound 19”,“Compound 20”, “Compound 21”, “Compound 22”, “Compound 23”, “Compound24”, “Compound 25”, “Compound 26”, “Compound 27” or “Compound 28”.

Test results indicate that the compounds of the present invention areobserved to be highly active preemergent and/or postemergent herbicidesand/or plant growth regulants. The compounds of the invention areobserved to generally show highest activity for postemergence weedcontrol (i.e. applied after weed seedlings emerge from the soil) andpreemergence weed control (i.e. applied before weed seedlings emergefrom the soil). Many of them are observed to have utility forbroad-spectrum pre- and/or postemergence weed control in areas wherecomplete control of all vegetation is desired such as around fuelstorage tanks, industrial storage areas, parking lots, drive-intheaters, air fields, river banks, irrigation and other waterways,around billboards and highway and railroad structures. Many of thecompounds of this invention, by virtue of selective metabolism in cropsversus weeds, or by selective activity at the locus of physiologicalinhibition in crops and weeds, or by selective placement on or withinthe environment of a mixture of crops and weeds, are observed to beuseful for the selective control of grass and broadleaf weeds within acrop/weed mixture. One skilled in the art will recognize that thepreferred combination of these selectivity factors within a compound orgroup of compounds can readily be determined by performing routinebiological and/or biochemical assays. Compounds of this invention areobserved to show tolerance to important agronomic crops including, butis not limited to, alfalfa, barley, cotton, wheat, rape, sugar beets,corn (maize), sorghum, soybeans, rice, oats, peanuts, vegetables,tomato, potato, perennial plantation crops including coffee, cocoa, oilpalm, rubber, sugarcane, citrus, grapes, fruit trees, nut trees, banana,plantain, pineapple, hops, tea and forests such as eucalyptus andconifers (e.g., loblolly pine), and turf species (e.g., Kentuckybluegrass, St. Augustine grass, Kentucky fescue and Bermuda grass).Compounds of this invention can be used in crops genetically transformedor bred to incorporate resistance to herbicides, express proteins toxicto invertebrate pests (such as Bacillus thuringiensis toxin), and/orexpress other useful traits. Those skilled in the art will appreciatethat not all compounds are equally effective against all weeds.Alternatively, the subject compounds are useful to modify plant growth.

As the compounds of the invention have both preemergent and postemergentherbicidal activity, to control undesired vegetation by killing orinjuring the vegetation or reducing its growth, the compounds can beusefully applied by a variety of methods involving contacting aherbicidally effective amount of a compound of the invention, or acomposition comprising said compound and at least one of a surfactant, asolid diluent or a liquid diluent, to the foliage or other part of theundesired vegetation or to the environment of the undesired vegetationsuch as the soil or water in which the undesired vegetation is growingor which surrounds the seed or other propagule of the undesiredvegetation.

A herbicidally effective amount of the compounds of this invention isdetermined by a number of factors. These factors include: formulationselected, method of application, amount and type of vegetation present,growing conditions, etc. In general, a herbicidally effective amount ofcompounds of this invention is about 0.001 to 20 kg/ha with a preferredrange of about 0.004 to 1 kg/ha. One skilled in the art can easilydetermine the herbicidally effective amount necessary for the desiredlevel of weed control.

In one common embodiment, a compound of the invention is applied,typically in a formulated composition, to a locus comprising desiredvegetation (e.g., crops) and undesired vegetation (i.e. weeds), both ofwhich may be seeds, seedlings and/or larger plants, in contact with agrowth medium (e.g., soil). In this locus, a composition comprising acompound of the invention can be directly applied to a plant or a partthereof, particularly of the undesired vegetation, and/or to the growthmedium in contact with the plant.

Plant varieties and cultivars of the desired vegetation in the locustreated with a compound of the invention can be obtained by conventionalpropagation and breeding methods or by genetic engineering methods.Genetically modified plants (transgenic plants) are those in which aheterologous gene (transgene) has been stably integrated into theplant's genome. A transgene that is defined by its particular locationin the plant genome is called a transformation or transgenic event.

Genetically modified plant cultivars in the locus which can be treatedaccording to the invention include those that are resistant against oneor more biotic stresses (pests such as nematodes, insects, mites, fungi,etc.) or abiotic stresses (drought, cold temperature, soil salinity,etc.), or that contain other desirable characteristics. Plants can begenetically modified to exhibit traits of, for example, herbicidetolerance, insect-resistance, modified oil profiles or droughttolerance. Useful genetically modified plants containing single genetransformation events or combinations of transformation events arelisted in Exhibit C. Additional information for the geneticmodifications listed in Exhibit C can be obtained from publiclyavailable databases maintained, for example, by the U.S. Department ofAgriculture.

The following abbreviations, T1 through T37, are used in Exhibit C fortraits. A “−” means the entry is not available; “tol.” means “tolerance”and “res.” means resistance.

Trait Description T1 Glyphosate tol. T2 High lauric acid oil T3Glufosinate tol. T4 Phytate breakdown T5 Oxynil tol. T6 Disease res. T7Insect res. T9 Modified flower color T11 ALS Herbicide tol. T12 Dicambatol. T13 Anti-allergy T14 Salt tol. T15 Cold tol. T16 Imidazolinoneherb. tol. T17 Modified alpha-amylase T18 Pollination control T19 2,4-Dtol. T20 Increased lysine T21 Drought tol. T22 Delayedripening/senescence T23 Modified product quality T24 High cellulose T25Modified starch/carbohydrate T26 Insect & disease resist. T27 Hightryptophan T28 Erect leaves semidwarf T29 Semidwarf T30 Low iron tol.T31 Modified oil/fatty acid T32 HPPD tol. T33 High oil T34Aryloxyalkanoate tol. T35 Mesotrione tol. T36 Reduced nicotine T37Modified product

Exhibit C Crop Event Name Event Code Trait(s) Gene(s) Alfalfa J101MON-00101-8 T1 cp4 epsps (aroA:CP4) Alfalfa J163 MON-ØØ163-7 T1 cp4epsps (aroA:CP4) Canola* 23-18-17 (Event 18) CGN-89465-2 T2 te Canola*23-198 (Event 23) CGN-89465-2 T2 te Canola* 61061 DP-Ø61Ø61-7 T1 gat4621Canola* 73496 DP-Ø73496-4 T1 gat4621 Canola* GT200 (RT200) MON-89249-2T1 cp4 epsps (aroA:CP4); goxv247 Canola* GT73 (RT73) MON-ØØØ73-7 T1 cp4epsps (aroA:CP4); goxv247 Canola* HCN10 (Topas 19/2) — T3 bar Canola*HCN28 (T45) ACS-BNØØ8-2 T3 pat (syn) Canola* HCN92 (Topas 19/2)ACS-BNØØ7-1 T3 bar Canola* MON88302 MON-883Ø2-9 T1 cp4 epsps (aroA:CP4)Canola* MPS961 — T4 phyA Canola* MPS962 — T4 phyA Canola* MPS963 — T4phyA Canola* MPS964 — T4 phyA Canola* MPS965 — T4 phyA Canola* MS1(B91-4) ACS-BNØØ4-7 T3 bar Canola* MS8 ACS-BNØØ5-8 T3 bar Canola*OXY-235 ACS-BNØ11-5 T5 bxn Canola* PHY14 — T3 bar Canola* PHY23 — T3 barCanola* PHY35 — T3 bar Canola* PHY36 — T3 bar Canola* RF1 (B93-101)ACS-BNØØ1-4 T3 bar Canola* RF2 (B94-2) ACS-BNØØ2-5 T3 bar Canola* RF3ACS-BNØØ3-6 T3 bar Bean EMBRAPA 5.1 EMB-PV051-1 T6 ac1 (sense andantisense) Brinjal # EE-1 — T7 cry1Ac Cotton 19-51a DD-Ø1951A-7 T11S4-HrA Cotton 281-24-236 DAS-24236-5 T3, T7 pat (syn); cry1F Cotton3006-210-23 DAS-21Ø23-5 T3, T7 pat (syn); cry1Ac Cotton 31707 — T5, T7bxn; cry1Ac Cotton 31803 — T5, T7 bxn; cry1Ac Cotton 31807 — T5, T7 bxn;cry1Ac Cotton 31808 — T5, T7 bxn; cry1Ac Cotton 42317 — T5, T7 bxn;cry1Ac Cotton BNLA-601 — T7 cry1Ac Cotton BXN10211 BXN10211-9 T5 bxn;cry1Ac Cotton BXN10215 BXN10215-4 T5 bxn; cry1Ac Cotton BXN10222BXN10222-2 T5 bxn; cry1Ac Cotton BXN10224 BXN10224-4 T5 bxn; cry1AcCotton COT102 SYN-IR102-7 T7 vip3A(a) Cotton COT67B SYN-IR67B-1 T7cry1Ab Cotton COT202 — T7 vip3A Cotton Event 1 — T7 cry1Ac Cotton GMFCry1A GTL-GMF311-7 T7 cry1Ab-Ac Cotton GHB119 BCS-GH005-8 T7 cry2AeCotton GHB614 BCS-GH002-5 T1 2mepsps Cotton GK12 — T7 cry1Ab-Ac CottonLLCotton25 ACS-GH001-3 T3 bar Cotton MLS 9124 — T7 cry1C Cotton MON1076MON-89924-2 T7 cry1Ac Cotton MON1445 MON-01445-2 T1 cp4 epsps (aroA:CP4)Cotton MON15985 MON-15985-7 T7 cry1Ac; cry2Ab2 Cotton MON1698MON-89383-1 T7 cp4 epsps (aroA:CP4) Cotton MON531 MON-00531-6 T7 cry1AcCotton MON757 MON-00757-7 T7 cry1Ac Cotton MON88913 MON-88913-8 T1 cp4epsps (aroA:CP4) Cotton Nqwe Chi 6 Bt — T7 — Cotton SKG321 — T7 cry1A;CpTI Cotton T303-3 BCS-GH003-6 T3, T7 cry1Ab; bar Cotton T304-40BCS-GH004-7 T3, T7 cry1Ab; bar Cotton CE43-67B — T7 cry1Ab CottonCE46-02A — T7 cry1Ab Cotton CE44-69D — T7 cry1Ab Cotton 1143-14A — T7cry1Ab Cotton 1143-51B — T7 cry1Ab Cotton T342-142 — T7 cry1Ab CottonPV-GHGT07 (1445) — T1 cp4 epsps (aroA:CP4) Cotton EE-GH3 — T1 mepspsCotton EE-GH5 — T7 cry1Ab Cotton MON88701 MON-88701-3 T3, T12 Modifieddmo; bar Cotton OsCr11 — T13 Modified Cry j Flax FP967 CDC-FL001-2 T11als Lentil RH44 — T16 als Maize 3272 SYN-E3272-5 T17 amy797E Maize 5307SYN-05307-1 T7 ecry3.1Ab Maize 59122 DAS-59122-7 T3, T7 cry34Ab1;cry35Ab1; pat Maize 676 PH-000676-7 T3, T18 pat; dam Maize 678PH-000678-9 T3, T18 pat; dam Maize 680 PH-000680-2 T3, T18 pat; damMaize 98140 DP-098140-6 T1, T11 gat4621; zm-hra Maize Bt10 — T3, T7cry1Ab; pat Maize Bt176 (176) SYN-EV176-9 T3, T7 cry1Ab; bar MaizeBVLA430101 — T4 phyA2 Maize CBH-351 ACS-ZM004-3 T3, T7 cry9C; bar MaizeDAS40278-9 DAS40278-9 T19 aad-1 Maize DBT418 DKB-89614-9 T3, T7 cry1Ac;pinII; bar Maize DLL25 (B16) DKB-89790-5 T3 bar Maize GA21 MON-00021-9T1 mepsps Maize GG25 — T1 mepsps Maize GJ11 — T1 mepsps Maize Fl117 — T1mepsps Maize GAT-ZM1 — T3 pat Maize LY038 REN-00038-3 T20 cordapA MaizeMIR162 SYN-IR162-4 T7 vip3Aa20 Maize MIR604 SYN-IR604-5 T7 mcry3A MaizeMON801 (MON80100) MON801 T1, T7 cry1Ab; cp4 epsps (aroA:CP4); goxv247Maize MON802 MON-80200-7 T1, T7 cry1Ab; cp4 epsps (aroA:CP4); goxv247Maize MON809 PH-MON-809-2 T1, T7 cry1Ab; cp4 epsps (aroA:CP4); goxv247Maize MON810 MON-00810-6 T1, T7 cry1Ab; cp4 epsps (aroA:CP4); goxv247Maize MON832 — T1 cp4 epsps (aroA:CP4); goxv247 Maize MON863 MON-00863-5T7 cry3Bb1 Maize MON87427 MON-87427-7 T1 cp4 epsps (aroA:CP4) MaizeMON87460 MON-87460-4 T21 cspB Maize MON88017 MON-88017-3 T1, T7 cry3Bb1;cp4 epsps (aroA:CP4) Maize MON89034 MON-89034-3 T7 cry2Ab2; cry1A.105Maize MS3 ACS-ZM001-9 T3, T18 bar; barnase Maize MS6 ACS-ZM005-4 T3, T18bar; barnase Maize NK603 MON-00603-6 T1 cp4 epsps (aroA:CP4) Maize T14ACS-ZM002-1 T3 pat (syn) Maize T25 ACS-ZM003-2 T3 pat (syn) Maize TC1507DAS-01507-1 T3, T7 cry1Fa2; pat Maize TC6275 DAS-06275-8 T3, T7 mocry1F;bar Maize VIP1034 — T3, T7 vip3A; pat Maize 43A47 DP-043A47-3 T3, T7cry1F; cry34Ab1; cry35Ab1; pat Maize 40416 DP-040416-8 T3, T7 cry1F;cry34Ab1; cry35Ab1; pat Maize 32316 DP-032316-8 T3, T7 cry1F; cry34Ab1;cry35Ab1; pat Maize 4114 DP-004114-3 T3, T7 cry1F; cry34Ab1; cry35Ab1;pat Melon Melon A — T22 sam-k Melon Melon B — T22 sam-k Papaya 55-1CUH-CP551-8 T6 prsv cp Papaya 63-1 CUH-CP631-7 T6 prsv cp Papaya HuanongNo. 1 — T6 prsv rep Papaya X17-2 UFL-X17CP-6 T6 prsv cp Plum C-5ARS-PLMC5-6 T6 ppv cp Canola** ZSR500 — T1 cp4 epsps (aroA:CP4); goxv247Canola** ZSR502 — T1 cp4 epsps (aroA:CP4); goxv247 Canola** ZSR503 — T1cp4 epsps (aroA:CP4); goxv247 Rice 7Crp#242-95-7 — T13 7crp Rice 7Crp#10— T13 7crp Rice GM Shanyou 63 — T7 cry1Ab; cry1Ac Rice Huahui-1/TT51-1 —T7 cry1Ab; cry1Ac Rice LLRICE06 ACS-OS001-4 T3 bar Rice LLRICE601BCS-OS003-7 T3 bar Rice LLRICE62 ACS-OS002-5 T3 bar Rice Tarom molaii +cry1Ab — T7 cry1Ab (truncated) Rice GAT-OS2 — T3 bar Rice GAT-OS3 — T3bar Rice PE-7 — T7 Cry1Ac Rice 7Crp#10 — T13 7crp Rice KPD627-8 — T27OASA1D Rice KPD722-4 — T27 OASA1D Rice KA317 — T27 OASA1D Rice HW5 — T27OASA1D Rice HW1 — T27 OASA1D Rice B-4-1-18 — T28 Δ OsBRI1 Rice G-3-3-22— T29 OSGA2ox1 Rice AD77 — T6 DEF Rice AD51 — T6 DEF Rice AD48 — T6 DEFRice AD41 — T6 DEF Rice 13pNasNa800725atAprt1 — T30 HvNAS1; HvNAAT-A;APRT Rice 13pAprt1 — T30 APRT Rice gHvNAS1-gHvNAAT-1 — T30 HvNAS1;HvNAAT-A; HvNAAT-B Rice gHvIDS3-1 — T30 HvIDS3 Rice gHvNAAT1 — T30HvNAAT-A; HvNAAT-B Rice gHvNAS1-1 — T30 HvNAS1 Rice NIA-OS006-4 — T6WRKY45 Rice NIA-OS005-3 — T6 WRKY45 Rice NIA-OS004-2 — T6 WRKY45 RiceNIA-OS003-1 — T6 WRKY45 Rice NIA-OS002-9 — T6 WRKY45 Rice NIA-OS001-8 —T6 WRKY45 Rice OsCr11 — T13 Modified Cry j Rice 17053 — T1 cp4 epsps(aroA:CP4) Rice 17314 — T2 cp4 epsps (aroA:CP4) Rose WKS82/130-4-1IFD-52401-4 T9 5AT; bp40 (f3′5′h) Rose WKS92/130-9-1 IFD-52901-9 T9 5AT;bp40 (f3′5′h) Soybean 260-05 (G94-1, G94-19, — T9 gm-fad2-1 (silencinglocus) G168) Soybean A2704-12 ACS-GM005-3 T3 pat Soybean A2704-21ACS-GM004-2 T3 pat Soybean A5547-127 ACS-GM006-4 T3 pat Soybean A5547-35ACS-GM008-6 T3 pat Soybean CV127 BPS-CV127-9 T16 csr1-2 SoybeanDAS68416-4 DAS68416-4 T3 pat Soybean DP305423 DP-305423-1 T11, T31gm-fad2-1 (silencing locus); gm-hra Soybean DP356043 DP-356043-5 T1, T31gm-fad2-1 (silencing locus); gat4601 Soybean FG72 MST-FG072-3 T32, T12mepsps; hppdPF W336 Soybean GTS 40-3-2 (40-3-2) MON-04032-6 T1 cp4epsps (aroA:CP4) Soybean GU262 ACS-GM003-1 T3 pat Soybean MON87701MON-87701-2 T7 cry1Ac Soybean MON87705 MON-87705-6 T1, T31 fatb1-A(sense & antisense); fad2-1A (sense & antisense); cp4 epsps (aroA:CP4)Soybean MON87708 MON-87708-9 T1, T12 dmo; cp4 epsps (aroA:CP4) SoybeanMON87769 MON-87769-7 T1, T31 Pj.D6D; Nc.Fad3; cp4 epsps (aroA:CP4)Soybean MON89788 MON-89788-1 T1 cp4 epsps (aroA:CP4) Soybean W62ACS-GM002-9 T3 bar Soybean W98 ACS-GM001-8 T3 bar Soybean MON87754MON-87754-1 T33 dgat2A Soybean DAS21606 DAS-21606 T34, T3 Modifiedaad-12; pat Soybean DAS44406 DAS-44406-6 T1, T3, T34 Modified aad-12;2mepsps; pat Soybean SYHT04R SYN-0004R-8 T35 Modified avhppd Soybean9582.814.19.1 — T3, T7 cry1Ac, cry1F, PAT Squash CZW3 SEM-ØCZW3-2 T6 cmvcp, zymv cp, wmv cp Squash ZW20 SEM-0ZW20-7 T6 zymv cp, wmv cp SugarBeet GTSB77 (T9100152) SY-GTSB77-8 T1 cp4 epsps (aroA:CP4); goxv247Sugar Beet H7-1 KM-000H71-4 T1 cp4 epsps (aroA:CP4) Sugar Beet T120-7ACS-BV001-3 T3 pat Sugar Beet T227-1 — T1 cp4 epsps (aroA:CP4) SugarcaneNXI-1T — T21 EcbetA Sunflower X81359 — T16 als Pepper PK-SP01 — T6 cmvcp Tobacco C/F/93/08-02 — T5 bxn Tobacco Vector 21-41 — T36 NtQPT1(antisense) Sunflower X81359 — T16 als Wheat MON71800 MON-718ØØ-3 T1 cp4epsps (aroA:CP4) *Argentine (Brassica napus), **Polish (B. rapa), #Eggplant

Although most typically, compounds of the invention are used to controlundesired vegetation, contact of desired vegetation in the treated locuswith compounds of the invention may result in super-additive orsynergistic effects with genetic traits in the desired vegetation,including traits incorporated through genetic modification. For example,resistance to phytophagous insect pests or plant diseases, tolerance tobiotic/abiotic stresses or storage stability may be greater thanexpected from the genetic traits in the desired vegetation.

Compounds of this invention can also be mixed with one or more otherbiologically active compounds or agents including herbicides, herbicidesafeners, fungicides, insecticides, nematocides, bactericides,acaricides, growth regulators such as insect molting inhibitors androoting stimulants, chemosterilants, semiochemicals, repellents,attractants, pheromones, feeding stimulants, plant nutrients, otherbiologically active compounds or entomopathogenic bacteria, virus orfungi to form a multi-component pesticide giving an even broaderspectrum of agricultural protection. Mixtures of the compounds of theinvention with other herbicides can broaden the spectrum of activityagainst additional weed species, and suppress the proliferation of anyresistant biotypes. Thus the present invention also pertains to acomposition comprising a compound of Formula 1 (in a herbicidallyeffective amount) and at least one additional biologically activecompound or agent (in a biologically effective amount) and can furthercomprise at least one of a surfactant, a solid diluent or a liquiddiluent. The other biologically active compounds or agents can beformulated in compositions comprising at least one of a surfactant,solid or liquid diluent. For mixtures of the present invention, one ormore other biologically active compounds or agents can be formulatedtogether with a compound of Formula 1, to form a premix, or one or moreother biologically active compounds or agents can be formulatedseparately from the compound of Formula 1, and the formulations combinedtogether before application (e.g., in a spray tank) or, alternatively,applied in succession.

A mixture of one or more of the following herbicides with a compound ofthis invention may be particularly useful for weed control: acetochlor,acifluorfen and its sodium salt, aclonifen, acrolein (2-propenal),alachlor, alloxydim, ametryn, amicarbazone, amidosulfuron,aminocyclopyrachlor and its esters (e.g., methyl, ethyl) and salts(e.g., sodium, potassium), aminopyralid, amitrole, ammonium sulfamate,anilofos, asulam, atrazine, azimsulfuron, beflubutamid, benazolin,benazolin-ethyl, bencarbazone, benfluralin, benfuresate,bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap,bicyclopyrone, bifenox, bilanafos, bispyribac and its sodium salt,bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil octanoate,butachlor, butafenacil, butamifos, butralin, butroxydim, butylate,cafenstrole, carbetamide, carfentrazone-ethyl, catechin, chlomethoxyfen,chloramben, chlorbromuron, chlorflurenol-methyl, chloridazon,chlorimuron-ethyl, chlorotoluron, chlorpropham, chlorsulfuron,chlorthal-dimethyl, chlorthiamid, cinidon-ethyl, cinmethylin,cinosulfuron, clacyfos, clefoxydim, clethodim, clodinafop-propargyl,clomazone, clomeprop, clopyralid, clopyralid-olamine,cloransulam-methyl, cumyluron, cyanazine, cycloate, cyclopyrimorate,cyclosulfamuron, cycloxydim, cyhalofop-butyl, 2,4-D and its butotyl,butyl, isoctyl and isopropyl esters and its dimethylammonium, diolamineand trolamine salts, daimuron, dalapon, dalapon-sodium, dazomet, 2,4-DBand its dimethylammonium, potassium and sodium salts, desmedipham,desmetryn, dicamba and its diglycolammonium, dimethylammonium, potassiumand sodium salts, dichlobenil, dichlorprop, diclofop-methyl, diclosulam,difenzoquat metilsulfate, diflufenican, diflufenzopyr, dimefuron,dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P,dimethipin, dimethylarsinic acid and its sodium salt, dinitramine,dinoterb, diphenamid, diquat dibromide, dithiopyr, diuron, DNOC,endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron-methyl,ethiozin, ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanid,fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenquinotrione,fentrazamide, fenuron, fenuron-TCA, flamprop-methyl,flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam,fluazifop-butyl, fluazifop-P-butyl, fluazolate, flucarbazone,flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl,flumetsulam, flumiclorac-pentyl, flumioxazin, fluometuron,fluoroglycofen-ethyl, flupoxam, flupyrsulfuron-methyl and its sodiumsalt, flurenol, flurenol-butyl, fluridone, flurochloridone, fluroxypyr,flurtamone, fluthiacet-methyl, fomesafen, foramsulfuron,fosamine-ammonium, glufosinate, glufosinate-ammonium, glufosinate-P,glyphosate and its salts such as ammonium, isopropylammonium, potassium,sodium (including sesquisodium) and trimesium (alternatively namedsulfosate), halauxifen, halauxifen-methyl, halosulfuron-methyl,haloxyfop-etotyl, haloxyfop-methyl, hexazinone, hydantocidin,imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin,imazaquin-ammonium, imazethapyr, imazethapyr-ammonium, imazosulfuron,indanofan, indaziflam, iofensulfuron, iodosulfuron-methyl, ioxynil,ioxynil octanoate, ioxynil-sodium, ipfencarbazone, isoproturon, isouron,isoxaben, isoxaflutole, isoxachlortole, lactofen, lenacil, linuron,maleic hydrazide, MCPA and its salts (e.g., MCPA-dimethylammonium,MCPA-potassium and MCPA-sodium, esters (e.g., MCPA-2-ethylhexyl,MCPA-butotyl) and thioesters (e.g., MCPA-thioethyl), MCPB and its salts(e.g., MCPB-sodium) and esters (e.g., MCPB-ethyl), mecoprop, mecoprop-P,mefenacet, mefluidide, mesosulfuron-methyl, mesotrione, metam-sodium,metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron,methylarsonic acid and its calcium, monoammonium, monosodium anddisodium salts, methyldymron, metobenzuron, metobromuron, metolachlor,S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron-methyl,molinate, monolinuron, naproanilide, napropamide, napropamide-M,naptalam, neburon, nicosulfuron, norflurazon, orbencarb,orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron,oxaziclomefone, oxyfluorfen, paraquat dichloride, pebulate, pelargonicacid, pendimethalin, penoxsulam, pentanochlor, pentoxazone, perfluidone,pethoxamid, pethoxyamid, phenmedipham, picloram, picloram-potassium,picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron-methyl,prodiamine, profoxydim, prometon, prometryn, propachlor, propanil,propaquizafop, propazine, propham, propisochlor, propoxycarbazone,propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil,pyraflufen-ethyl, pyrasulfotole, pyrazogyl, pyrazolynate, pyrazoxyfen,pyrazosulfuron-ethyl, pyribenzoxim, pyributicarb, pyridate, pyriftalid,pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium,pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine,quizalofop-ethyl, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron,saflufenacil, sethoxydim, siduron, simazine, simetryn, sulcotrione,sulfentrazone, sulfometuron-methyl, sulfosulfuron, 2,3,6-TBA, TCA,TCA-sodium, tebutam, tebuthiuron, tefuryltrione, tembotrione,tepraloxydim, terbacil, terbumeton, terbuthylazine, terbutryn,thenylchlor, thiazopyr, thiencarbazone, thifensulfuron-methyl,thiobencarb, tiafenacil, tiocarbazil, tolpyralate, topramezone,tralkoxydim, tri-allate, triafamone, triasulfuron, triaziflam,tribenuron-methyl, triclopyr, triclopyr-butotyl,triclopyr-triethylammonium, tridiphane, trietazine, trifloxysulfuron,trifludimoxazin, trifluralin, triflusulfuron-methyl, tritosulfuron,vernolate,3-(2-chloro-3,6-difluorophenyl)-4-hydroxy-1-methyl-1,5-naphthyridin-2(1H)-one,5-chloro-3-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-1-(4-methoxyphenyl)-2(1H)-quinoxalinone,2-chloro-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)-3-pyridinecarboxamide,7-(3,5-dichloro-4-pyridinyl)-5-(2,2-difluoroethyl)-8-hydroxypyrido[2,3-b]pyrazin-6(5H)-one),4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone),5-[[(2,6-difluorophenyl)methoxy]methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)isoxazole(previously methioxolin),4-(4-fluorophenyl)-6-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-methyl-1,2,4-triazine-3,5(2H,4H)-dione,methyl4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylate,2-methyl-3-(methylsulfonyl)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamideand2-methyl-N-(4-methyl-1,2,5-oxadiazol-3-yl)-3-(methylsulfinyl)-4-(trifluoromethyl)benzamide.Other herbicides also include bioherbicides such as Alternaria destruensSimmons, Colletotrichum gloeosporiodes (Penz.) Penz. & Sacc., Drechsieramonoceras (MTB-951), Myrothecium verrucaria (Albertini & Schweinitz)Ditmar: Fries, Phytophthora palmivora (Butl.) Butl. and Pucciniathlaspeos Schub.

Compounds of this invention can also be used in combination with plantgrowth regulators such as aviglycine, N-(phenylmethyl)-1H-purin-6-amine,epocholeone, gibberellic acid, gibberellin A₄ and A₇, harpin protein,mepiquat chloride, prohexadione calcium, prohydrojasmon, sodiumnitrophenolate and trinexapac-methyl, and plant growth modifyingorganisms such as Bacillus cereus strain BP01.

General references for agricultural protectants (i.e. herbicides,herbicide safeners, insecticides, fungicides, nematocides, acaricidesand biological agents) include The Pesticide Manual, 13th Edition, C. D.S. Tomlin, Ed., British Crop Protection Council, Farnham, Surrey, U. K.,2003 and The BioPesticide Manual, 2nd Edition, L. G. Copping, Ed.,British Crop Protection Council, Farnham, Surrey, U. K., 2001.

For embodiments where one or more of these various mixing partners areused, the mixing partners are typically used in the amounts similar toamounts customary when the mixture partners are used alone. Moreparticularly in mixtures, active ingredients are often applied at anapplication rate between one-half and the full application ratespecified on product labels for use of active ingredient alone. Theseamounts are listed in references such as The Pesticide Manual and TheBioPesticide Manual. The weight ratio of these various mixing partners(in total) to the compound of Formula 1 is typically between about1:3000 and about 3000:1. Of note are weight ratios between about 1:300and about 300:1 (for example ratios between about 1:30 and about 30:1).One skilled in the art can easily determine through simpleexperimentation the biologically effective amounts of active ingredientsnecessary for the desired spectrum of biological activity. It will beevident that including these additional components may expand thespectrum of weeds controlled beyond the spectrum controlled by thecompound of Formula 1 alone.

In certain instances, combinations of a compound of this invention withother biologically active (particularly herbicidal) compounds or agents(i.e. active ingredients) can result in a greater-than-additive (i.e.synergistic) effect on weeds and/or a less-than-additive effect (i.e.safening) on crops or other desirable plants. Reducing the quantity ofactive ingredients released in the environment while ensuring effectivepest control is always desirable. Ability to use greater amounts ofactive ingredients to provide more effective weed control withoutexcessive crop injury is also desirable. When synergism of herbicidalactive ingredients occurs on weeds at application rates givingagronomically satisfactory levels of weed control, such combinations canbe advantageous for reducing crop production cost and decreasingenvironmental load. When safening of herbicidal active ingredientsoccurs on crops, such combinations can be advantageous for increasingcrop protection by reducing weed competition.

Of note is a combination of a compound of the invention with at leastone other herbicidal active ingredient. Of particular note is such acombination where the other herbicidal active ingredient has differentsite of action from the compound of the invention. In certain instances,a combination with at least one other herbicidal active ingredienthaving a similar spectrum of control but a different site of action willbe particularly advantageous for resistance management. Thus, acomposition of the present invention can further comprise (in aherbicidally effective amount) at least one additional herbicidal activeingredient having a similar spectrum of control but a different site ofaction.

Compounds of this invention can also be used in combination withherbicide safeners such as allidochlor, benoxacor, cloquintocet-mexyl,cumyluron, cyometrinil, cyprosulfonamide, daimuron, dichlormid,dicyclonon, dietholate, dimepiperate, fenchlorazole-ethyl, fenclorim,flurazole, fluxofenim, furilazole, isoxadifen-ethyl, mefenpyr-diethyl,mephenate, methoxyphenone naphthalic anhydride (1,8-naphthalicanhydride), oxabetrinil, N-(aminocarbonyl)-2-methylbenzenesulfonamide,N-(aminocarbonyl)-2-fluorobenzenesulfonamide,1-bromo-4-[(chloromethyl)sulfonyl]benzene (BCS),4-(dichloroacetyl)-1-oxa-4-azospiro[4.5]decane (MON 4660),2-(dichloromethyl)-2-methyl-1,3-dioxolane (MG 191), ethyl1,6-dihydro-1-(2-methoxyphenyl)-6-oxo-2-phenyl-5-pyrimidinecarboxylate,2-hydroxy-N,N-dimethyl-6-(trifluoromethyl)pyridine-3-carboxamide, and3-oxo-1-cyclohexen-1-yl1-(3,4-dimethylphenyl)-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinecarboxylate,2,2-dichloro-1-(2,2,5-trimethyl-3-oxazolidinyl)-ethanone and2-methoxy-N-[[4-[[(methylamino)carbonyl]amino]phenyl]sulfonyl]-benzamideto increase safety to certain crops. Antidotally effective amounts ofthe herbicide safeners can be applied at the same time as the compoundsof this invention, or applied as seed treatments. Therefore an aspect ofthe present invention relates to a herbicidal mixture comprising acompound of this invention and an antidotally effective amount of aherbicide safener. Seed treatment is particularly useful for selectiveweed control, because it physically restricts antidoting to the cropplants. Therefore a particularly useful embodiment of the presentinvention is a method for selectively controlling the growth ofundesired vegetation in a crop comprising contacting the locus of thecrop with a herbicidally effective amount of a compound of thisinvention wherein seed from which the crop is grown is treated with anantidotally effective amount of safener. Antidotally effective amountsof safeners can be easily determined by one skilled in the art throughsimple experimentation.

Compounds of the invention cans also be mixed with: (1) polynucleotidesincluding but not limited to DNA, RNA, and/or chemically modifiednucleotides influencing the amount of a particular target through downregulation, interference, suppression or silencing of the geneticallyderived transcript that render a herbicidal effect; or (2)polynucleotides including but not limited to DNA, RNA, and/or chemicallymodified nucleotides influencing the amount of a particular targetthrough down regulation, interference, suppression or silencing of thegenetically derived transcript that render a safening effect.

Of note is a composition comprising a compound of the invention (in aherbicidally effective amount), at least one additional activeingredient selected from the group consisting of other herbicides andherbicide safeners (in an effective amount), and at least one componentselected from the group consisting of surfactants, solid diluents andliquid diluents.

Table A1 lists specific combinations of a Component (a) with Component(b) illustrative of the mixtures, compositions and methods of thepresent invention. Compound 1 in the Component (a) column is identifiedin Index Table A. The second column of Table A1 lists the specificComponent (b) compound (e.g., “2,4-D” in the first line). The third,fourth and fifth columns of Table A1 lists ranges of weight ratios forrates at which the Component (a) compound is typically applied to afield-grown crop relative to Component (b) (i.e. (a):(b)). Thus, forexample, the first line of Table A1 specifically discloses thecombination of Component (a) (i.e. Compound 1 in Index Table A throughD) with 2,4-D is typically applied in a weight ratio between 1:192-6:1.The remaining lines of Table A1 are to be construed similarly.

TABLE A1 Component (a) Typical More Typical Most Typical (Compound #)Component (b) Weight Ratio Weight Ratio Weight Ratio 1 2,4-D 1:192-6:11:64-2:1 1:24-1:3 1 Acetochlor 1:768-2:1 1:256-1:2   1:96-1:11 1Acifluorfen  1:96-12:1 1:32-4:1 1:12-1:2 1 Aclonifen 1:857-2:11:285-1:3  1:107-1:12 1 Alachlor 1:768-2:1 1:256-1:2   1:96-1:11 1Ametryn 1:384-3:1 1:128-1:1  1:48-1:6 1 Amicarbazone 1:192-6:1 1:64-2:11:24-1:3 1 Amidosulfuron   1:6-168:1  1:2-56:1  1:1-11:1 1Aminocyclopyrachlor  1:48-24:1 1:16-8:1  1:6-2:1 1 Aminopyralid 1:20-56:1  1:6-19:1  1:2-4:1 1 Amitrole 1:768-2:1 1:256-1:2   1:96-1:111 Anilofos  1:96-12:1 1:32-4:1 1:12-1:2 1 Asulam 1:960-2:1 1:320-1:3 1:120-1:14 1 Atrazine 1:192-6:1 1:64-2:1 1:24-1:3 1 Azimsulfuron  1:6-168:1  1:2-56:1  1:1-11:1 1 Beflubutamid 1:342-4:1 1:114-2:1 1:42-1:5 1 Benfuresate 1:617-2:1 1:205-1:2  1:77-1:9 1Bensulfuron-methyl  1:25-45:1  1:8-15:1  1:3-3:1 1 Bentazone 1:192-6:11:64-2:1 1:24-1:3 1 Benzobicyclon  1:85-14:1 1:28-5:1 1:10-1:2 1Benzofenap 1:257-5:1 1:85-2:1 1:32-1:4 1 Bicyclopyrone  1:42-27:11:14-9:1  1:5-2:1 1 Bifenox 1:257-5:1 1:85-2:1 1:32-1:4 1Bispyribac-sodium   1:10-112:1  1:3-38:1  1:1-7:1 1 Bromacil 1:384-3:11:128-1:1  1:48-1:6 1 Bromobutide 1:384-3:1 1:128-1:1  1:48-1:6 1Bromoxynil  1:96-12:1 1:32-4:1 1:12-1:2 1 Butachlor 1:768-2:1 1:256-1:2  1:96-1:11 1 Butafenacil  1:42-27:1 1:14-9:1  1:5-2:1 1 Butylate1:1542-1:2  1:514-1:5  1:192-1:22 1 Carfenstrole 1:192-6:1 1:64-2:11:24-1:3 1 Carfentrazone-ethyl 1:128-9:1 1:42-3:1 1:16-1:2 1Chlorimuron-ethyl   1:8-135:1  1:2-45:1  1:1-9:1 1 Chlorotoluron1:768-2:1 1:256-1:2   1:96-1:11 1 Chlorsulfuron   1:6-168:1  1:2-56:1 1:1-11:1 1 Cincosulfuron  1:17-68:1  1:5-23:1  1:2-5:1 1 Cinidon-ethyl1:384-3:1 1:128-1:1  1:48-1:6 1 Cinmethylin  1:34-34:1  1:11-12:1 1:4-3:1 1 Clacyfos  1:34-34:1  1:11-12:1  1:4-3:1 1 Clethodim 1:48-24:1 1:16-8:1  1:6-2:1 1 Clodinafop-propargyl  1:20-56:1  1:6-19:1 1:2-4:1 1 Clomazone 1:384-3:1 1:128-1:1  1:48-1:6 1 Clomeprop 1:171-7:11:57-3:1 1:21-1:3 1 Clopyralid 1:192-6:1 1:64-2:1 1:24-1:3 1Cloransulam-methyl  1:12-96:1  1:4-32:1  1:1-6:1 1 Cumyluron 1:384-3:11:128-1:1  1:48-1:6 1 Cyanazine 1:384-3:1 1:128-1:1  1:48-1:6 1Cyclopyrimorate  1:17-68:1  1:5-23:1  1:2-5:1 1 Cyclosulfamuron 1:17-68:1  1:5-23:1  1:2-5:1 1 Cycloxydim  1:96-12:1 1:32-4:1 1:12-1:21 Cyhalofop  1:25-45:1  1:8-15:1  1:3-3:1 1 Daimuron 1:192-6:1 1:64-2:11:24-1:3 1 Desmedipham 1:322-4:1 1:107-2:1  1:40-1:5 1 Dicamba 1:192-6:11:64-2:1 1:24-1:3 1 Dichlobenil 1:1371-1:2  1:457-1:4  1:171-1:20 1Dichlorprop 1:925-2:1 1:308-1:3  1:115-1:13 1 Diclofop-methyl 1:384-3:11:128-1:1  1:48-1:6 1 Diclosulam   1:10-112:1  1:3-38:1  1:1-7:1 1Difenzoquat 1:288-4:1 1:96-2:1 1:36-1:4 1 Diflufenican 1:857-2:11:285-1:3  1:107-1:12 1 Diflufenzopyr  1:12-96:1  1:4-32:1  1:1-6:1 1Dimethachlor 1:768-2:1 1:256-1:2   1:96-1:11 1 Dimethametryn 1:192-6:11:64-2:1 1:24-1:3 1 Dimethenamid-P 1:384-3:1 1:128-1:1  1:48-1:6 1Dithiopyr 1:192-6:1 1:64-2:1 1:24-1:3 1 Diuron 1:384-3:1 1:128-1:1 1:48-1:6 1 EPTC 1:768-2:1 1:256-1:2   1:96-1:11 1 Esprocarb 1:1371-1:2 1:457-1:4  1:171-1:20 1 Ethalfluralin 1:384-3:1 1:128-1:1  1:48-1:6 1Ethametsulfuron-methyl  1:17-68:1  1:5-23:1  1:2-5:1 1 Ethoxyfen  1:8-135:1  1:2-45:1  1:1-9:1 1 Ethoxysulfuron  1:20-56:1  1:6-19:1 1:2-4:1 1 Etobenzanid 1:257-5:1 1:85-2:1 1:32-1:4 1 Fenoxaprop-ethyl 1:120-10:1 1:40-4:1 1:15-1:2 1 Fenoxasulfone  1:85-14:1 1:28-5:11:10-1:2 1 Fenquinotrione  1:17-68:1  1:5-23:1  1:2-5:1 1 Fentrazamide 1:17-68:1  1:5-23:1  1:2-5:1 1 Flazasulfuron  1:17-68:1  1:5-23:1 1:2-5:1 1 Florasulam   1:2-420:1   1:1-140:1  2:1-27:1 1Fluazifop-butyl 1:192-6:1 1:64-2:1 1:24-1:3 1 Flucarbazone   1:8-135:1 1:2-45:1  1:1-9:1 1 Flucetosulfuron   1:8-135:1  1:2-45:1  1:1-9:1 1Flufenacet 1:257-5:1 1:85-2:1 1:32-1:4 1 Flumetsulam  1:24-48:1 1:8-16:1  1:3-3:1 1 Flumiclorac-pentyl   1:10-112:1  1:3-38:1  1:1-7:11 Flumioxazin  1:25-45:1  1:8-15:1  1:3-3:1 1 Fluometuron 1:384-3:11:128-1:1  1:48-1:6 1 Flupyrsulfuron-methyl   1:3-336:1   1:1-112:1 2:1-21:1 1 Fluridone 1:384-3:1 1:128-1:1  1:48-1:6 1 Fluroxypyr 1:96-12:1 1:32-4:1 1:12-1:2 1 Flurtamone 1:857-2:1 1:285-1:3 1:107-1:12 1 Fluthiacet-methyl  1:48-42:1  1:16-14:1  1:3-3:1 1Fomesafen  1:96-12:1 1:32-4:1 1:12-1:2 1 Foramsulfuron  1:13-84:1 1:4-28:1  1:1-6:1 1 Glufosinate 1:288-4:1 1:96-2:1 1:36-1:4 1Glyphosate 1:288-4:1 1:96-2:1 1:36-1:4 1 Halosulfuron-methyl  1:17-68:1 1:5-23:1  1:2-5:1 1 Halauxifen  1:20-56:1  1:6-19:1  1:2-4:1 1Halauxifen-methyl  1:20-56:1  1:6-19:1  1:2-4:1 1 Haloxyfop-methyl 1:34-34:1  1:11-12:1  1:4-3:1 1 Hexazinone 1:192-6:1 1:64-2:1 1:24-1:31 Hydantocidin 1:1100-16:1 1:385-8:1  1:144-4:1  1 Imazamox  1:13-84:1 1:4-28:1  1:1-6:1 1 Imazapic  1:20-56:1  1:6-19:1  1:2-4:1 1 Imazapyr 1:85-14:1 1:28-5:1 1:10-1:2 1 Imazaquin  1:34-34:1  1:11-12:1  1:4-3:11 Imazethabenz-methyl 1:171-7:1 1:57-3:1 1:21-1:3 1 Imazethapyr 1:24-48:1  1:8-16:1  1:3-3:1 1 Imazosulfuron  1:27-42:1  1:9-14:1 1:3-3:1 1 Indanofan 1:342-4:1 1:114-2:1  1:42-1:5 1 Indaziflam 1:25-45:1  1:8-15:1  1:3-3:1 1 Iodosulfuron-methyl   1:3-336:1  1:1-112:1  2:1-21:1 1 Ioxynil 1:192-6:1 1:64-2:1 1:24-1:3 1Ipfencarbazone  1:85-14:1 1:28-5:1 1:10-1:2 1 Isoproturon 1:384-3:11:128-1:1  1:48-1:6 1 Isoxaben 1:288-4:1 1:96-2:1 1:36-1:4 1Isoxaflutole  1:60-20:1 1:20-7:1  1:7-2:1 1 Lactofen  1:42-27:1 1:14-9:1 1:5-2:1 1 Lenacil 1:384-3:1 1:128-1:1  1:48-1:6 1 Linuron 1:384-3:11:128-1:1  1:48-1:6 1 MCPA 1:192-6:1 1:64-2:1 1:24-1:3 1 MCPB 1:288-4:11:96-2:1 1:36-1:4 1 Mecoprop 1:768-2:1 1:256-1:2   1:96-1:11 1 Mefenacet1:384-3:1 1:128-1:1  1:48-1:6 1 Mefluidide 1:192-6:1 1:64-2:1 1:24-1:3 1Mesosulfuron-methyl   1:5-224:1  1:1-75:1  1:1-14:1 1 Mesotrione 1:42-27:1 1:14-9:1  1:5-2:1 1 Metamifop  1:42-27:1 1:14-9:1  1:5-2:1 1Metazachlor 1:384-3:1 1:128-1:1  1:48-1:6 1 Metazosulfuron  1:25-45:1 1:8-15:1  1:3-3:1 1 Methabenzthiazuron 1:768-2:1 1:256-1:2   1:96-1:111 Metolachlor 1:768-2:1 1:256-1:2   1:96-1:11 1 Metosulam   1:8-135:1 1:2-45:1  1:1-9:1 1 Metribuzin 1:192-6:1 1:64-2:1 1:24-1:3 1Metsulfuron-methyl   1:2-560:1   1:1-187:1  3:1-35:1 1 Molinate1:1028-2:1  1:342-1:3  1:128-1:15 1 Napropamide 1:384-3:1 1:128-1:1 1:48-1:6 1 Napropamide-M 1:192-6:1 1:64-2:1 1:24-1:3 1 Naptalam1:192-6:1 1:64-2:1 1:24-1:3 1 Nicosulfuron  1:12-96:1  1:4-32:1  1:1-6:11 Norflurazon 1:1152-1:1  1:384-1:3  1:144-1:16 1 Orbencarb 1:1371-1:2 1:457-1:4  1:171-1:20 1 Orthosulfamuron  1:20-56:1  1:6-19:1  1:2-4:1 1Oryzalin 1:514-3:1 1:171-1:2  1:64-1:8 1 Oxadiargyl 1:384-3:1 1:128-1:1 1:48-1:6 1 Oxadiazon 1:548-3:1 1:182-1:2  1:68-1:8 1 Oxasulfuron 1:27-42:1  1:9-14:1  1:3-3:1 1 Oxaziclomefone  1:42-27:1 1:14-9:1 1:5-2:1 1 Oxyfluorfen 1:384-3:1 1:128-1:1  1:48-1:6 1 Paraquat1:192-6:1 1:64-2:1 1:24-1:3 1 Pendimethalin 1:384-3:1 1:128-1:1 1:48-1:6 1 Penoxsulam   1:10-112:1  1:3-38:1  1:1-7:1 1 Penthoxamid1:384-3:1 1:128-1:1  1:48-1:6 1 Pentoxazone  1:102-12:1 1:34-4:11:12-1:2 1 Phenmedipham  1:102-12:1 1:34-4:1 1:12-1:2 1 Picloram 1:96-12:1 1:32-4:1 1:12-1:2 1 Picolinafen  1:34-34:1  1:11-12:1 1:4-3:1 1 Pinoxaden  1:25-45:1  1:8-15:1  1:3-3:1 1 Pretilachlor1:192-6:1 1:64-2:1 1:24-1:3 1 Primisulfuron-methyl   1:8-135:1  1:2-45:1 1:1-9:1 1 Prodiamine 1:384-3:1 1:128-1:1  1:48-1:6 1 Profoxydim 1:42-27:1 1:14-9:1  1:5-2:1 1 Prometryn 1:384-3:1 1:128-1:1  1:48-1:6 1Propachlor 1:1152-1:1  1:384-1:3  1:144-1:16 1 Propanil 1:384-3:11:128-1:1  1:48-1:6 1 Propaquizafop  1:48-24:1 1:16-8:1  1:6-2:1 1Propoxycarbazone  1:17-68:1  1:5-23:1  1:2-5:1 1 Propyrisulfuron 1:17-68:1  1:5-23:1  1:2-5:1 1 Propyzamide 1:384-3:1 1:128-1:1 1:48-1:6 1 Prosulfocarb 1:1200-1:2  1:400-1:4  1:150-1:17 1 Prosulfuron  1:6-168:1  1:2-56:1  1:1-11:1 1 Pyraclonil  1:42-27:1 1:14-9:1 1:5-2:1 1 Pyraflufen-ethyl   1:5-224:1  1:1-75:1  1:1-14:1 1Pyrasulfotole  1:13-84:1  1:4-28:1  1:1-6:1 1 Pyrazolynate 1:857-2:11:285-1:3  1:107-1:12 1 Pyrazosulfuron-ethyl   1:10-112:1  1:3-38:1 1:1-7:1 1 Pyrazoxyfen   1:5-224:1  1:1-75:1  1:1-14:1 1 Pyribenzoxim  1:10-112:1  1:3-38:1  1:1-7:1 1 Pyributicarb 1:384-3:1 1:128-1:1 1:48-1:6 1 Pyridate 1:288-4:1 1:96-2:1 1:36-1:4 1 Pyriftalid  1:10-112:1  1:3-38:1  1:1-7:1 1 Pyriminobac-methyl  1:20-56:1 1:6-19:1  1:2-4:1 1 Pyrimisulfan  1:17-68:1  1:5-23:1  1:2-5:1 1Pyrithiobac  1:24-48:1  1:8-16:1  1:3-3:1 1 Pyroxasulfone  1:85-14:11:28-5:1 1:10-1:2 1 Pyroxsulam   1:5-224:1  1:1-75:1  1:1-14:1 1Quinclorac 1:192-6:1 1:64-2:1 1:24-1:3 1 Quizalofop-ethyl  1:42-27:11:14-9:1  1:5-2:1 1 Rimsulfuron  1:13-84:1  1:4-28:1  1:1-6:1 1Saflufenacil  1:25-45:1  1:8-15:1  1:3-3:1 1 Sethoxydim  1:96-12:11:32-4:1 1:12-1:2 1 Simazine 1:384-3:1 1:128-1:1  1:48-1:6 1 Sulcotrione 1:120-10:1 1:40-4:1 1:15-1:2 1 Sulfentrazone 1:147-8:1 1:49-3:11:18-1:3 1 Sulfometuron-methyl  1:34-34:1  1:11-12:1  1:4-3:1 1Sulfosulfuron   1:8-135:1  1:2-45:1  1:1-9:1 1 Tebuthiuron 1:384-3:11:128-1:1  1:48-1:6 1 Tefuryltrione  1:42-27:1 1:14-9:1  1:5-2:1 1Tembotrione  1:31-37:1  1:10-13:1  1:3-3:1 1 Tepraloxydim  1:25-45:1 1:8-15:1  1:3-3:1 1 Terbacil 1:288-4:1 1:96-2:1 1:36-1:4 1Terbuthylazine 1:857-2:1 1:285-1:3  1:107-1:12 1 Terbutryn 1:192-6:11:64-2:1 1:24-1:3 1 Thenylchlor  1:85-14:1 1:28-5:1 1:10-1:2 1 Thiazopyr1:384-3:1 1:128-1:1  1:48-1:6 1 Thiencarbazone   1:3-336:1   1:1-112:1 2:1-21:1 1 Thifensulfuron-methyl   1:5-224:1  1:1-75:1  1:1-14:1 1Tiafenacil  1:17-68:1  1:5-23:1  1:2-5:1 1 Thiobencarb 1:768-2:11:256-1:2   1:96-1:11 1 Tolpyralate  1:31-37:1  1:10-13:1  1:3-3:1 1Topramzone   1:6-168:1  1:2-56:1  1:1-11:1 1 Tralkoxydim  1:68-17:11:22-6:1  1:8-2:1 1 Triafamone   1:2-420:1   1:1-140:1  2:1-27:1 1Triallate 1:768-2:1 1:256-1:2   1:96-1:11 1 Triasulfuron   1:5-224:1 1:1-75:1  1:1-14:1 1 Triaziflam 1:171-7:1 1:57-3:1 1:21-1:3 1Tribenuron-methyl   1:3-336:1   1:1-112:1  2:1-21:1 1 Triclopyr1:192-6:1 1:64-2:1 1:24-1:3 1 Trifloxysulfuron   1:2-420:1   1:1-140:1 2:1-27:1 1 Trifludimoxazin  1:25-45:1  1:8-15:1  1:3-3:1 1 Trifluralin1:288-4:1 1:96-2:1 1:36-1:4 1 Triflusulfuron-methyl  1:17-68:1  1:5-23:1 1:2-5:1 1 Tritosulfuron  1:13-84:1  1:4-28:1  1:1-6:1

Table A2 is constructed the same as Table A1 above except that entriesbelow the “Component (a)” column heading are replaced with therespective Component (a) Column Entry shown below. Compound 1 in theComponent (a) column is identified in Index Table A. Thus, for example,in Table A2 the entries below the “Component (a)” column heading allrecite “Compound 2” (i.e. Compound 2 identified in Index Table A), andthe first line below the column headings in Table A2 specificallydiscloses a mixture of Compound 2 with 2,4-D. Tables A3 through A7 areconstructed similarly.

Table Number Component (a) Column Entries A2 Compound 2 A3 Compound 3 A4Compound 4 A5 Compound 5 A6 Compound 6 A7 Compound 7 A8 Compound 8 A9Compound 9 A10 Compound 10 A11 Compound 11 A12 Compound 12 A13 Compound13 A14 Compound 14 A15 Compound 15 A16 Compound 16 A17 Compound 17 A18Compound 18 A19 Compound 19 A20 Compound 20 A21 Compound 21 A22 Compound22 A23 Compound 23 A24 Compound 24 A25 Compound 25 A26 Compound 26 A27Compound 27 A28 Compound 28

Preferred for better control of undesired vegetation (e.g., lower userate such as from synergism, broader spectrum of weeds controlled, orenhanced crop safety) or for preventing the development of resistantweeds are mixtures of a compound of this invention with a herbicideselected from the group consisting of chlorimuron-ethyl, nicosulfuron,mesotrione, thifensulfuron-methyl, flupyrsulfuron-methyl, tribenuron,pyroxasulfone, pinoxaden, tembotrione, pyroxsulam, metolachlor andS-metolachlor.

The following Tests demonstrate the control efficacy of the compounds ofthis invention against specific weeds. The weed control afforded by thecompounds is not limited, however, to these species. See Index Tables Athrough D for compound descriptions. The abbreviation “Cmpd. No.” standsfor “Compound Number”. The abbreviation “Ex.” stands for “Example” andis followed by a number indicating in which Synthesis Example thecompound is prepared. Mass spectra (MS) are reported with an estimatedprecision within ±0.5 Da as the molecular weight of the highest isotopicabundance parent ion (M+1) formed by addition of H+ (molecular weightof 1) to the molecule, or (M−1) formed by the loss of H+ (molecularweight of 1) from the molecule, observed by using liquid chromatographycoupled to a mass spectrometer (LCMS) using either atmospheric pressurechemical ionization (AP+) where “amu” stands for unified atomic massunits.

INDEX TABLE A

Cmpd. No. Q¹ Q² M.S. (AP+) 1 Ph(3-CF₃) Ph(2-F) 406.4

INDEX TABLE B

Cmpd. No. Q¹ Q² R³ m.p. (° C.)  2 (Ex. 1) Ph(3-CF₃) Ph(2-F) H **  5Ph(4-Cl) Ph(2,3-di-F) CH₃ 389.5 (M + 1)  6 Ph(4-CF₃) Ph(2-CF₃) CH₃ 455.5(M + 1)  7 Ph(4-Cl) Ph(2,3-di-F) H 375.4 (M + 1)  8 (Ex. 4) Ph(4-CF₃)Ph(2,3-di-F) CH₂CH₃ 437.5 (M + 1)  9 Ph(4-CH₂CH₃) Ph(3-F,2-CH₃) CH₃379.6 (M + 1) 10 Ph(3,4-di-CH₃) Ph(3-F,2-CH₃) CH₃ 379.6 (M + 1) 11Ph(4-CH₂CH₃) Ph(2,3-di-F) H 369.5 (M + 1) 12 Ph(4-CF₃) Ph(2,3-di-F) H409.5 (M + 1) 13 Ph(4-CH₃) Ph(2-F) H 337.2 (M + 1) 14 Ph(3,4-di-CH₃)Ph(2-SCH₃) CH₃ 393.6 (M + 1) 15 Ph(4-CH₂CH₃) Ph(2-SCH₃) CH₃ 393.6(M + 1) 16 Ph(3,4-di-CH₃) Ph(2,3-di-F) H 369.5 (M + 1) 17 Ph(4-CF₃)Ph(2,3-di-F) n-Pr 451.6 (M + 1) 18 Ph(3,4-di-CH₃) Ph(2-SCH₃) H 379.6(M + 1) 19 Ph(3,4-di-CH₃) Ph(2,3-di-F) CH₃ 383.5 (M + 1) 20 Ph(4-Cl)Ph(6-F) H 357.4 (M + 1) 21 Ph(4-Cl) Ph(2-F) CH₃ 371.5 (M + 1) 22 (Ex. 5)Ph(4-CF₃) Ph(2,3-di-F) CF₃ 477.5 (M + 1) 23 Ph(4-CH₂CH₃) Ph(2,3-di-F)CH₃ 383.5 (M + 1) 24 (Ex. 3) Ph(4-CF₃) Ph(2-F) CH₃ 405.5 (M + 1) 25Ph(4-CH₂CH₃) Ph(2-SCH₃) H 379.5 (M + 1) 26 Ph(3,4-di-CH₃) Ph(3-F,2-CH₃)H 365.6 (M + 1) 27 Ph(4-CH₃) Ph(2-F) CH₃ 351.5 (M + 1) 28 Ph(4-CH₂CH₃)Ph(3-F,2-CH₃) H 365.6 (M + 1) ** See Synthesis Example for ¹H NMR data.

INDEX TABLE C

Cmpd. No. Q¹ Q² m.p. (° C.) 3 (Ex. 2) Ph(3-CF₃) Ph(2-F) ** ** SeeSynthesis Example for ¹H NMR data.

INDEX TABLE D

Cmpd. No. Q¹ Q² M.S. (AP+) 4 Ph(3-CF₃) Ph(2-F) 390

Biological Examples of the Invention

Test A

Seeds of plant species selected from barnyardgrass (Echinochloacrus-galli), kochia (Kochia scoparia), ragweed (common ragweed, Ambrosiaelation), ryegrass, Italian (Italian ryegrass, Lolium multiflorum),foxtail, giant (giant foxtail, Setaria faberii), and pigweed (Amaranthusretroflexus), were planted into a blend of loam soil and sand andtreated preemergence with a directed soil spray using test chemicalsformulated in a non-phytotoxic solvent mixture which included asurfactant.

At the same time, plants selected from these weed species and alsoblackgrass (Alopecurus myosuroides), galium (catchweed bedstraw, Galiumaparine), wheat (Triticum aestivum), and corn (Zea mays) were planted inpots containing the same blend of loam soil and sand and treated withpostemergence applications of test chemicals formulated in the samemanner. Plants ranged in height from 2 to 10 cm and were in the one- totwo-leaf stage for the postemergence treatment. Treated plants anduntreated controls were maintained in a greenhouse for approximately 10d, after which time all treated plants were compared to untreatedcontrols and visually evaluated for injury. Plant response ratings,summarized in Table A, are based on a 0 to 100 scale where 0 is noeffect and 100 is complete control. A dash (-) response means no testresult.

TABLE A Compounds Compounds 500 g ai/ha 1 2 3 4 125 g ai/ha 1 2 3 4Postemergence Barnyardgrass 60 80 30 60 Barnyardgrass 0 60 0 20Blackgrass 0 70 0 40 Blackgrass 0 40 0 20 Corn 20 40 0 0 Corn 0 20 0 0Foxtail, Giant 40 90 50 70 Foxtail, Giant 0 50 20 20 Galium 0 50 0 0Galium 0 50 0 0 Kochia 0 30 0 0 Kochia 0 0 0 0 Pigweed 0 10 0 0 Pigweed0 0 0 0 Ragweed 0 10 0 0 Ragweed 0 0 0 0 Ryegrass, Italian 0 50 10 0Ryegrass, Italian 0 0 0 0 Wheat 0 50 0 20 Wheat 0 0 0 0 Compounds 500 gai/ha 5 6 7 8 9 10 11 12 13 14 15 Postemergence Barnyardgrass 80 40 7050 70 90 80 90 90 20 0 Blackgrass 20 20 0 0 70 70 20 60 40 20 0 Corn 300 30 0 0 40 30 60 20 0 0 Foxtail, Giant 80 30 70 60 50 80 70 90 80 20 0Galium 70 30 50 50 20 50 50 70 40 0 0 Kochia 30 0 40 40 0 30 50 60 30 00 Pigweed 20 0 50 60 0 0 0 70 0 0 0 Ragweed 20 0 60 20 0 20 30 50 30 0 0Ryegrass, Italian 20 20 20 0 20 30 50 60 0 0 0 Wheat 20 0 20 0 0 30 2040 0 0 0 Compounds 500 g ai/ha 16 17 18 19 20 21 22 23 24 25 26 27 28Postemergence Barnyardgrass 80 30 30 90 60 40 0 90 80 30 80 90 80Blackgrass 60 20 0 70 0 20 0 20 50 0 50 20 40 Corn 70 0 0 30 80 0 0 2040 0 0 0 0 Foxtail, Giant 80 30 20 80 70 70 0 70 80 30 80 90 60 Galium50 50 20 50 50 50 0 30 60 0 0 40 30 Kochia 30 50 20 20 40 0 0 30 0 30 00 50 Pigweed 0 40 0 0 0 0 0 0 20 0 0 0 0 Ragweed 50 0 0 20 20 0 0 0 0 00 0 0 Ryegrass, Italian 50 0 0 20 0 20 0 0 20 0 20 30 50 Wheat 50 0 0 3020 0 0 0 30 0 0 0 0 Compounds 125 g ai/ha 5 6 7 8 9 10 11 12 13 14 15Postemergence Barnyardgrass 20 0 20 20 30 50 70 30 50 0 0 Blackgrass 0 00 0 20 0 0 0 20 0 0 Corn 20 0 20 0 0 20 0 0 0 0 0 Foxtail, Giant 30 0 2020 0 30 40 30 60 0 0 Galium 40 0 40 30 0 0 20 30 40 0 0 Kochia 0 0 0 0 00 40 20 0 0 0 Pigweed 0 0 0 20 0 0 0 0 0 0 0 Ragweed 0 0 0 0 0 0 0 0 0 00 Ryegrass, Italian 0 0 0 0 0 0 0 0 0 0 0 Wheat 0 0 0 0 0 30 0 0 0 0 0Compounds 125 g ai/ha 16 17 18 19 20 21 22 23 24 25 26 27 28Postemergence Barnyardgrass 60 0 0 60 20 0 0 50 30 20 50 40 50Blackgrass 0 0 0 0 0 0 0 0 0 0 0 0 20 Corn 0 0 0 0 20 0 0 0 0 0 20 0 0Foxtail, Giant 60 0 0 30 20 0 0 30 40 0 50 30 40 Galium 40 40 20 0 30 00 0 0 0 30 0 20 Kochia 30 20 20 0 0 0 0 30 0 30 0 0 20 Pigweed 0 0 0 0 00 0 0 0 0 0 0 0 Ragweed 0 0 0 0 0 0 0 0 0 0 0 0 0 Ryegrass, Italian 0 00 0 0 0 0 0 0 0 0 0 0 Wheat 0 0 0 0 0 0 0 0 0 0 30 0 0 CompoundsCompounds 500 g ai/ha 1 2 3 4 125 g ai/ha 1 2 3 4 PreemergenceBarnyardgrass 70 90 60 90 Barnyardgrass 0 60 0 20 Foxtail, Giant 60 9080 90 Foxtail, Giant 0 90 0 60 Kochia 0 0 0 0 Kochia 0 0 0 0 Pigweed 0 00 0 Pigweed 0 0 0 0 Ragweed 0 0 0 0 Ragweed 0 0 0 0 Ryegrass, Italian 00 0 0 Ryegrass, Italian 0 0 0 0 Compounds 500 g ai/ha 5 6 7 8 9 10 11 1213 14 15 Preemergence Barnyardgrass 80 40 70 70 70 90 90 80 70 30 0Foxtail, Giant 90 90 80 90 90 90 90 90 90 60 0 Kochia 50 0 40 — 0 50 7080 70 0 0 Pigweed 0 40 20 50 0 20 30 80 0 0 0 Ragweed 40 0 50 0 0 0 4050 80 0 0 Ryegrass, Italian 30 60 0 0 0 70 30 60 0 0 0 Compounds 500 gai/ha 16 17 18 19 20 21 22 23 24 25 26 27 28 Preemergence Barnyardgrass90 50 60 90 70 40 20 90 40 40 90 90 90 Foxtail, Giant 90 90 80 90 90 7030 90 90 40 90 90 90 Kochia 80 30 0 30 90 40 0 40 60 20 30 0 60 Pigweed0 20 0 0 0 0 0 20 20 0 0 0 0 Ragweed 50 0 30 0 50 0 0 0 30 0 0 0 30Ryegrass, Italian 60 0 20 20 0 40 0 0 30 0 50 20 30 Compounds 125 gai/ha 5 6 7 8 9 10 11 12 13 14 15 Preemergence Barnyardgrass 30 0 30 3040 50 70 20 60 0 0 Foxtail, Giant 50 0 40 30 60 80 80 90 70 0 0 Kochia 00 0 0 0 0 60 30 70 0 0 Pigweed 0 0 0 20 0 0 30 30 0 0 0 Ragweed 0 0 0 00 0 0 0 0 0 0 Ryegrass, Italian 20 40 0 0 0 0 0 40 0 0 0 Compounds 125 gai/ha 16 17 18 19 20 21 22 23 24 25 26 27 28 Preemergence Barnyardgrass70 0 20 50 20 0 0 60 0 0 60 0 60 Foxtail, Giant 90 30 0 70 30 0 0 70 300 80 80 70 Kochia 70 0 0 0 30 0 0 20 0 0 20 0 60 Pigweed 0 0 0 0 0 0 0 00 0 0 0 0 Ragweed 0 0 0 0 0 0 0 0 0 0 0 0 0 Ryegrass, Italian 0 0 0 0 040 0 0 0 0 0 20 0Test B

Plant species in the flooded paddy test selected from rice (Oryzasativa), sedge, umbrella (small-flower umbrella sedge, Cyperusdifformis), ducksalad (Heteranthera limosa), and barnyardgrass(Echinochloa crus-galli) were grown to the 2-leaf stage for testing. Attime of treatment, test pots were flooded to 3 cm above the soilsurface, treated by application of test compounds directly to the paddywater, and then maintained at that water depth for the duration of thetest. Treated plants and controls were maintained in a greenhouse for 13to 15 days, after which time all species were compared to controls andvisually evaluated. Plant response ratings, summarized in Table B, arebased on a scale of 0 to 100 where 0 is no effect and 100 is completecontrol. A dash (-) response means no test result.

TABLE B Compounds Compound 500 g ai/ha 2 4 250 g ai/ha 1 FloodBarnyardgrass 0 0 Barnyardgrass 0 Ducksalad 0 0 Ducksalad 70 Rice 0 0Rice 0 Sedge, Umbrella 0 0 Sedge, Umbrella 50 Compounds 250 g ai/ha 5 67 8 9 10 11 12 13 14 15 16 17 Flood Barnyardgrass 40 0 0 0 20 20 0 0 4020 0 50 0 Ducksalad 20 0 50 40 75 45 95 75 45 60 50 75 30 Rice 0 0 15 015 0 0 0 20 0 20 15 0 Sedge, Umbrella 0 0 0 0 0 0 70 0 0 0 0 0 0Compounds 250 g ai/ha 18 19 20 21 22 23 24 25 26 27 28 FloodBarnyardgrass 0 30 40 0 0 0 0 0 0 0 40 Ducksalad 40 20 70 40 30 80 0 6585 70 90 Rice 0 0 0 0 0 0 0 0 20 0 20 Sedge, Umbrella 0 0 0 0 0 0 0 0 00 75

What is claimed is:
 1. A compound selected from Formula 1, N-oxides,stereoisomers and salts thereof,

wherein Q¹ is a phenyl or benzyl ring or a naphthalenyl ring, each ringoptionally substituted with up to 5 substituents independently selectedfrom R⁹; or a 5- to 6-membered fully unsaturated heterocyclic ring or an8- to 10-membered heteroaromatic bicyclic ring system, each ring or ringsystem containing ring members selected from carbon atoms and 1 to 4heteroatoms independently selected from up to 2 O, up to 2 S and up to 4N atoms, wherein up to 3 carbon ring members are independently selectedfrom C(═O) and C(═S), and the sulfur atom ring members are independentlyselected from S(═O)_(u)(═NR⁸)_(v), each ring or ring system optionallysubstituted with up to 5 substituents independently selected from R⁹ oncarbon atom ring members and selected from R¹⁰ on nitrogen atom ringmembers; Q² is a phenyl ring or a naphthalenyl ring, each ringoptionally substituted with up to 5 substituents independently selectedfrom R¹¹; or a 5- to 6-membered fully unsaturated heterocyclic ring oran 8- to 10-membered heteroaromatic bicyclic ring system, each ring orring system containing ring members selected from carbon atoms and 1 to4 heteroatoms independently selected from up to 2 O, up to 2 S and up to4 N atoms, wherein up to 3 carbon ring members are independentlyselected from C(═O) and C(═S), and the sulfur atom ring members areindependently selected from S(═O)_(u)(═NR⁸)_(v), each ring or ringsystem optionally substituted with up to 5 substituents independentlyselected from R¹¹ on carbon atom ring members and selected from R¹² onnitrogen atom ring members; R¹ and R² are each independently H, halogen,hydroxy or C₁-C₄ alkyl; Y is O, S or NR¹⁵; A is a saturated, partiallyunsaturated or fully unsaturated chain containing 2 to 4 atoms selectedfrom up to 4 carbon, up to 1 O, up to 1 S and up to 2 N atoms, whereinup to 2 carbon members are independently selected from C(═O) and C(═S)and the sulfur atom member is selected from S(═O)_(u)(═NR⁸)_(v); thesaid chain optionally substituted with up to 5 substituentsindependently selected from R³ on carbon atoms and R⁴ on nitrogen atoms;each R³ is independently halogen, cyano, hydroxy, —CO₂H, C₁-C₄ alkyl,C₁-C₄ haloalkyl, C₁-C₄ alkoxy, C₁-C₄ alkylthio, C₁-C₄ haloalkoxy, C₂-C₄alkoxyalkyl, C₂-C₄ alkylcarbonyl, C₂-C₄ alkoxycarbonyl, C₃-C₆ cycloalkylor C₄-C₆ cycloalkylalkyl; or two R³ are taken together with the carbonatom(s) to which they are bonded to form a C₃-C₇ cycloalkyl ring; eachR⁴ is independently cyano, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy,C₂-C₄ alkylcarbonyl, C₂-C₄ alkoxycarbonyl or C₃-C₆ cycloalkyl; J is—CR⁵R⁶— or —CR⁵R⁶—CR^(5a)R^(6a)— wherein the —CR⁵R⁶— moiety is directlyconnected to N; R⁵ and R⁶ are each independently H, halogen, hydroxy,C₁-C₄ alkyl or C₁-C₄ alkoxy; or R⁵ and R⁶ are taken together with thecarbon atom to which they are bonded to form a C₃-C₇ cycloalkyl ring;R^(5a) and R^(6a) are each independently H, halogen or C₁-C₄ alkyl; orR^(5a) and R^(6a) are taken together with the carbon atom to which theyare bonded to form a C₃-C₇ cycloalkyl ring; R⁷ is H, hydroxy, amino,C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₃-C₆ alkynyl, C₂-C₈alkoxyalkyl, C₂-C₈ haloalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈alkylsulfinylalkyl, C₂-C₈ alkylsulfonylalkyl, C₂-C₈ alkylcarbonyl, C₂-C₈haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, C₂-C₈ alkoxycarbonyl,C₂-C₈ haloalkoxycarbonyl, C₄-C₁₀ cycloalkoxycarbonyl, C₂-C₈alkylaminocarbonyl, C₃-C₁₀ dialkylaminocarbonyl, C₄-C₁₀cycloalkylaminocarbonyl, C₁-C₆ alkoxy, C₁-C₆ alkylthio, C₁-C₆haloalkylthio, C₃-C₈ cycloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₃-C₈ cycloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆haloalkylsulfonyl, C₃-C₈ cycloalkylsulfonyl, C₁-C₆ alkylaminosulfonyl,C₂-C₈ dialkylaminosulfonyl, C₃-C₁₀ trialkylsilyl or G¹; each R⁸ isindependently H, cyano, C₂-C₃ alkylcarbonyl or C₂-C₃ haloalkylcarbonyl;each R⁹ is independently halogen, cyano, nitro, C₁-C₈ alkyl, C₁-C₄cyanoalkyl, C₁-C₄ cyanoalkoxy, C₁-C₈ haloalkyl, C₁-C₈ nitroalkyl, C₂-C₈alkenyl, C₂-C₈ haloalkenyl, C₂-C₈ nitroalkenyl, C₂-C₈ alkynyl, C₂-C₈haloalkynyl, C₄-C₁₀ cycloalkylalkyl, C₄-C₁₀ halocycloalkylalkyl, C₅-C₁₂alkylcycloalkylalkyl, C₅-C₁₂ cycloalkylalkenyl, C₅-C₁₂cycloalkylalkynyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₄-C₁₀alkylcycloalkyl, C₆-C₁₂ cycloalkylcycloalkyl, C₃-C₈ cycloalkenyl, C₃-C₈halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₂-C₈ haloalkoxyalkyl, C₃-C₈haloalkoxyalkoxy, C₁-C₄ hydroxyalkyl, C₄-C₁₀ cycloalkoxyalkyl, C₃-C₁₀alkoxyalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈alkylsulfonylalkyl, C₂-C₈ alkylaminoalkyl, C₂-C₈ haloalkylaminoalkyl,C₄-C₁₀ cycloalkylaminoalkyl, C₃-C₁₀ dialkylaminoalkyl, —CHO, C₂-C₈alkylcarbonyl, C₂-C₈ haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl,—C(═O)OH, C₂-C₈ alkoxycarbonyl, C₂-C₈ haloalkoxycarbonyl, C₄-C₁₀cycloalkoxycarbonyl, C₅-C₁₂ cycloalkylalkoxycarbonyl, —C(═O)NH₂, C₂-C₈alkylaminocarbonyl, C₄-C₁₀ cycloalkylaminocarbonyl, C₃-C₁₀dialkylaminocarbonyl, C₁-C₈ alkoxy, C₁-C₈ haloalkoxy, C₂-C₈alkoxyalkoxy, C₂-C₈ alkenyloxy, C₂-C₈ haloalkenyloxy, C₂-C₈haloalkoxyhaloalkoxy, C₃-C₈ alkynyloxy, C₃-C₈ haloalkynyloxy, C₃-C₈cycloalkoxy, C₃-C₈ halocycloalkoxy, C₄-C₁₀ cycloalkylalkoxy, C₃-C₁₀alkylcarbonylalkoxy, C₂-C₈ alkylcarbonyloxy, C₂-C₈ haloalkylcarbonyloxy,C₄-C₁₀ cycloalkylcarbonyloxy, C₁-C₈ alkylsulfonyloxy, C₁-C₈haloalkylsulfonyloxy, C₁-C₈ alkylthio, C₁-C₈ haloalkylthio, C₃-C₈cycloalkylthio, C₁-C₈ alkylsulfinyl, C₁-C₈ haloalkylsulfinyl, C₁-C₈alkylsulfonyl, C₁-C₈ haloalkylsulfonyl, C₃-C₈ cycloalkylsulfonyl,formylamino, C₂-C₈ alkylcarbonylamino, C₂-C₈ haloalkylcarbonylamino,C₂-C₈ alkoxycarbonylamino, C₁-C₆ alkylsulfonylamino, C₁-C₆haloalkylsulfonylamino, —SF₅, —SCN, SO₂NH₂, C₃-C₁₂ trialkylsilyl, C₄-C₁₂trialkylsilylalkyl, C₄-C₁₂ trialkylsilylalkoxy or G²; each R¹¹ isindependently halogen, cyano, nitro, C₁-C₈ alkyl, C₁-C₄ cyanoalkyl,C₁-C₄ cyanoalkoxy, C₁-C₈ haloalkyl, C₁-C₈ nitroalkyl, C₂-C₈ alkenyl,C₂-C₈ haloalkenyl, C₂-C₈ nitroalkenyl, C₂-C₈ alkynyl, C₂-C₈ haloalkynyl,C₄-C₁₀ cycloalkylalkyl, C₄-C₁₀ halocycloalkylalkyl, C₅-C₁₂alkylcycloalkylalkyl, C₅-C₁₂ cycloalkylalkenyl, C₅-C₁₂cycloalkylalkynyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₄-C₁₀alkylcycloalkyl, C₆-C₁₂ cycloalkylcycloalkyl, C₃-C₈ cycloalkenyl, C₃-C₈halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₂-C₈ haloalkoxyalkyl, C₃-C₈haloalkoxyalkoxy, C₁-C₄ hydroxyalkyl, C₄-C₁₀ cycloalkoxyalkyl, C₃-C₁₀alkoxyalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈alkylsulfonylalkyl, C₂-C₈ alkylaminoalkyl, C₂-C₈ haloalkylaminoalkyl,C₄-C₁₀ cycloalkylaminoalkyl, C₃-C₁₀ dialkylaminoalkyl, —CHO, C₂-C₈alkylcarbonyl, C₂-C₈ haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl,—C(═O)OH, C₂-C₈ alkoxycarbonyl, C₂-C₈ haloalkoxycarbonyl, C₄-C₁₀cycloalkoxycarbonyl, C₅-C₁₂ cycloalkylalkoxycarbonyl, —C(═O)NH₂, C₂-C₈alkylaminocarbonyl, C₄-C₁₀ cycloalkylaminocarbonyl, C₃-C₁₀dialkylaminocarbonyl, C₁-C₈ alkoxy, C₁-C₈ haloalkoxy, C₂-C₈alkoxyalkoxy, C₂-C₈ alkenyloxy, C₂-C₈ haloalkenyloxy, C₂-C₈haloalkoxyhaloalkoxy, C₃-C₈ alkynyloxy, C₃-C₈ haloalkynyloxy, C₃-C₈cycloalkoxy, C₃-C₈ halocycloalkoxy, C₄-C₁₀ cycloalkylalkoxy, C₃-C₁₀alkylcarbonylalkoxy, C₂-C₈ alkylcarbonyloxy, C₂-C₈ haloalkylcarbonyloxy,C₄-C₁₀ cycloalkylcarbonyloxy, C₁-C₈ alkylsulfonyloxy, C₁-C₈haloalkylsulfonyloxy, C₁-C₈ alkylthio, C₁-C₈ haloalkylthio, C₃-C₈cycloalkylthio, C₁-C₈ alkylsulfinyl, C₁-C₈ haloalkylsulfinyl, C₁-C₈alkylsulfonyl, C₁-C₈ haloalkylsulfonyl, C₃-C₈ cycloalkylsulfonyl,formylamino, C₂-C₈ alkylcarbonylamino, C₂-C₈ haloalkylcarbonylamino,C₂-C₈ alkoxycarbonylamino, C₁-C₆ alkylsulfonylamino, C₁-C₆haloalkylsulfonylamino, —SF₅, —SCN, SO₂NH₂, C₃-C₁₂ trialkylsilyl, C₄-C₁₂trialkylsilylalkyl, C₄-C₁₂ trialkylsilylalkoxy or G³; each R¹⁰ and R¹²is independently cyano, C₁-C₃ alkyl, C₂-C₃ alkenyl, C₂-C₃ alkynyl, C₃-C₆cycloalkyl, C₂-C₃ alkoxyalkyl, C₁-C₃ alkoxy, C₂-C₃ alkylcarbonyl, C₂-C₃alkoxycarbonyl, C₂-C₃ alkylaminoalkyl or C₃-C₄ dialkylaminoalkyl; R¹⁵ isH, cyano, C₁-C₄ alkyl, C₁-C₄ haloalkyl, —(C═O)CH₃ or —(C═O)CF₃; each G¹is independently phenyl, phenylmethyl, pyridinylmethyl, pyridinyloxy,phenylcarbonyl, phenoxy, phenylethynyl, phenylsulfonyl,phenylcarbonyl(C₁-C₄ alkyl); or a 5- or 6-membered heteroaromatic ring,each optionally substituted on ring members with up to 5 substituentsindependently selected from R¹³; each G² is independently phenyl,phenylmethyl, pyridinylmethyl, phenylcarbonyl, phenylcarbonylalkyl,phenoxy, phenylethynyl, phenylsulfonyl or pyridyloxy; or a 5- or6-membered heteroaromatic ring, each optionally substituted on ringmembers with up to 5 substituents independently selected from R¹⁴; orR¹⁶ON═CR¹⁷—, (R¹⁸)₂C═NO—, (R¹⁹)₂NN═CR¹⁷—, (R¹⁸)₂C═NNR²O—, R²¹N═CR¹⁷—,(R¹⁸)₂C═N—, R²²ON═CR¹⁷C(R²³)₂— or (R¹⁸)₂C═NOC(R²³)₂—, wherein the freebond projecting to the right indicates the connecting point to Q¹; eachG³ is independently phenyl, phenylmethyl, pyridinylmethyl,phenylcarbonyl, phenylcarbonylalkyl, phenoxy, phenylethynyl,phenylsulfonyl or pyridyloxy; or a 5- or 6-membered heteroaromatic ring,each optionally substituted on ring members with up to 5 substituentsindependently selected from R¹⁵; each R¹³, R¹⁴ and R¹⁵ is independentlyhalogen, cyano, hydroxy, amino, nitro, —CHO, —C(═O)OH, —C(═O)NH₂,—SO₂NH₂, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl,C₂-C₈ alkylcarbonyl, C₂-C₈ haloalkylcarbonyl, C₂-C₈ alkoxycarbonyl,C₄-C₁₀ cycloalkoxycarbonyl, C₅-C₁₂ cycloalkylalkoxycarbonyl, C₂-C₈alkylaminocarbonyl, C₃-C₁₀ dialkylaminocarbonyl, C₁-C₆ alkoxy, C₁-C₆haloalkoxy, C₂-C₈ alkylcarbonyloxy, C₁-C₆ alkylthio, C₁-C₆haloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₁-C₆ alkylaminosulfonyl, C₂-C₈dialkylaminosulfonyl, C₃-C₁₀ trialkylsilyl, C₁-C₆ alkylamino, C₂-C₈dialkylamino, C₂-C₈ alkylcarbonylamino or C₁-C₆ alkylsulfonylamino; eachR¹⁶ is independently H, C₁-C₆ alkyl, C₃-C₈ cycloalkyl, C₄-C₈cycloalkylalkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₃-C₆ alkynyl, C₂-C₈alkoxyalkyl, C₂-C₈ haloalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈alkylsulfinylalkyl, C₂-C₈ alkylsulfonylalkyl, C₂-C₈ alkylcarbonyl, C₂-C₈haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, C₂-C₈ alkoxycarbonyl,C₂-C₈ haloalkoxycarbonyl, C₄-C₁₀ cycloalkoxycarbonyl, C₂-C₈alkylaminocarbonyl, C₃-C₁₀ dialkylaminocarbonyl, C₄-C₁₀cycloalkylaminocarbonyl, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl,C₃-C₈ cycloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl,C₃-C₈ cycloalkylsulfonyl, C₁-C₆ alkylaminosulfonyl, C₂-C₈dialkylaminosulfonyl, C₃-C₁₀ trialkylsilyl or G¹; each R¹⁷ isindependently H, C₁-C₆ alkyl, C₃-C₈ cycloalkyl, C₄-C₈ cycloalkylalkyl,C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₃-C₆ alkynyl, C₂-C₈ alkoxyalkyl, C₂-C₈haloalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈alkylsulfonylalkyl, C₁-C₆ alkoxy, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio,C₃-C₈ cycloalkylthio, C₃-C₁₀ trialkylsilyl or G¹; each R¹⁸ isindependently H, hydroxy, C₁-C₆ alkyl, C₃-C₈ cycloalkyl, C₄-C₈cycloalkylalkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₃-C₆ alkynyl, C₂-C₈alkoxyalkyl, C₂-C₈ haloalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈alkylsulfinylalkyl, C₂-C₈ alkylsulfonylalkyl, C₂-C₈ alkylcarbonyl, C₂-C₈haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, C₂-C₈ alkoxycarbonyl,C₂-C₈ haloalkoxycarbonyl, C₄-C₁₀ cycloalkoxycarbonyl, C₂-C₈alkylaminocarbonyl, C₃-C₁₀ dialkylaminocarbonyl, C₄-C₁₀cycloalkylaminocarbonyl, C₁-C₆ alkoxy, C₁-C₆ alkylthio, C₁-C₆haloalkylthio, C₃-C₈ cycloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₃-C₈ cycloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆haloalkylsulfonyl, C₃-C₈ cycloalkylsulfonyl, C₁-C₆ alkylaminosulfonyl,C₂-C₈ dialkylaminosulfonyl, C₃-C₁₀ trialkylsilyl or G¹; each R¹⁹ isindependently H, C₁-C₆ alkyl, C₃-C₈ cycloalkyl, C₄-C₈ cycloalkylalkyl,C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₃-C₆ alkynyl, C₂-C₈ alkoxyalkyl, C₂-C₈haloalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈alkylsulfonylalkyl, C₂-C₈ alkylcarbonyl, C₂-C₈ haloalkylcarbonyl, C₄-C₁₀cycloalkylcarbonyl, C₂-C₈ alkoxycarbonyl, C₂-C₈ haloalkoxycarbonyl,C₄-C₁₀ cycloalkoxycarbonyl, C₂-C₈ alkylaminocarbonyl, C₃-C₁₀dialkylaminocarbonyl, C₄-C₁₀ cycloalkylaminocarbonyl, C₁-C₆ alkoxy,C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₃-C₈ cycloalkylsulfinyl,C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₃-C₈ cycloalkylsulfonyl,C₁-C₆ alkylaminosulfonyl, C₂-C₈ dialkylaminosulfonyl, C₃-C₁₀trialkylsilyl or G¹; each R²⁰ is independently H, C₁-C₆ alkyl, C₃-C₈cycloalkyl, C₄-C₈ cycloalkylalkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₃-C₆alkynyl, C₂-C₈ alkoxyalkyl, C₂-C₈ haloalkoxyalkyl, C₂-C₈ alkylthioalkyl,C₂-C₈ alkylsulfinylalkyl, C₂-C₈ alkylsulfonylalkyl, C₁-C₆ alkoxy, C₃-C₁₀trialkylsilyl or G¹; each R²¹ is independently H, hydroxy, amino, C₁-C₆alkyl, C₃-C₈ cycloalkyl, C₄-C₈ cycloalkylalkyl, C₁-C₆ haloalkyl, C₂-C₆alkenyl, C₃-C₆ alkynyl, C₂-C₈ alkoxyalkyl, C₂-C₈ haloalkoxyalkyl, C₂-C₈alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈ alkylsulfonylalkyl,C₂-C₈ alkylcarbonyl, C₂-C₈ haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl,C₂-C₈ alkoxycarbonyl, C₂-C₈ haloalkoxycarbonyl, C₄-C₁₀cycloalkoxycarbonyl, C₂-C₈ alkylaminocarbonyl, C₃-C₁₀dialkylaminocarbonyl, C₄-C₁₀ cycloalkylaminocarbonyl, C₁-C₆ alkoxy,C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₃-C₈ cycloalkylsulfinyl,C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₃-C₈ cycloalkylsulfonyl,C₁-C₆ alkylaminosulfonyl, C₂-C₈ dialkylaminosulfonyl, C₃-C₁₀trialkylsilyl or G¹; each R²² is independently H, C₁-C₄ alkyl, C₃-C₈cycloalkyl, C₄-C₈ cycloalkylalkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy, C₁-C₄haloalkoxy, C₂-C₄ alkoxyalkyl, C₂-C₄ alkylcarbonyl, C₂-C₄ alkoxycarbonylor C₃-C₆ cycloalkyl; each R²³ is independently H, halogen, cyano,hydroxy, C₁-C₄ alkyl, C₃-C₈ cycloalkyl, C₄-C₈ cycloalkylalkyl, C₁-C₄haloalkyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₂-C₄ alkoxyalkyl, C₂-C₄alkylcarbonyl, C₂-C₄ alkoxycarbonyl or C₃-C₆ cycloalkyl; and each u andv are independently 0, 1 or 2 in each instance of S(═O)u(=NR8)v,provided that the sum of u and v is 0, 1 or 2; and provided the compoundis other than a compound of Formula 1 wherein Q¹ is Ph(3-CF₃); Q² isPh(2-F); R¹ is H; R² is H; Y is O; A is —CH₂CH₂—; J is —CR⁵R⁶—; R⁵ is H;R⁶ is H; and R⁷ is H.
 2. The compound of claim 1 wherein Q¹ is a phenylor benzyl ring or a naphthalenyl ring, each ring optionally substitutedwith up to 5 substituents independently selected from R⁹; or a 5- to6-membered fully unsaturated heterocyclic ring, each ring containingring members selected from carbon atoms and 1 to 4 heteroatomsindependently selected from up to 2 O, up to 2 S and up to 4 N atoms,wherein up to 3 carbon ring members are independently selected fromC(═O) and C(═S), and the sulfur atom ring members are independentlyselected from S(═O)_(u)(═NR⁸)_(v), each ring optionally substituted withup to 5 substituents independently selected from R⁹ on carbon atom ringmembers and selected from R¹⁰ on nitrogen atom ring members; Q² is aphenyl ring or a naphthalenyl ring, each ring optionally substitutedwith up to 5 substituents independently selected from R¹¹; or a 5- to6-membered fully unsaturated heterocyclic ring, each ring containingring members selected from carbon atoms and 1 to 4 heteroatomsindependently selected from up to 1 O, up to 1 S and up to 2 N atoms,wherein up to 2 carbon ring members are independently selected fromC(═O) and C(═S), and the sulfur atom ring members are independentlyselected from S(═O)_(u)(═NR⁸)_(v), each ring optionally substituted withup to 5 substituents independently selected from R¹¹ on carbon atom ringmembers and selected from R¹² on nitrogen atom ring members; R¹ and R²are each independently H, halogen or C₁-C₄ alkyl; Y is O or S; A is asaturated, partially unsaturated or fully unsaturated chain containing 2to 4 atoms selected from up to 3 carbon, up to 1 O, up to 1 S and up to1 N atoms, wherein up to 2 carbon members are independently selectedfrom C(═O) and C(═S) and the sulfur atom member is selected fromS(═O)_(u)(═NR⁸)_(v); the said chain optionally substituted with up to 3substituents independently selected from R³ on carbon atoms and R⁴ onnitrogen atoms; each R³ is independently halogen, cyano, hydroxy, —CO₂H,C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy, C₁-C₄ alkylthio, C₃-C₆cycloalkyl or C₄-C₆ cycloalkylalkyl; each R⁴ is independently C₁-C₄alkyl, C₁-C₄ haloalkyl or C₃-C₆ cycloalkyl; R⁵ and R⁶ are eachindependently H, halogen, hydroxy or CH₃; R^(5a) and R^(6a) are eachindependently H or C₁-C₄ alkyl; R⁷ is H, hydroxy, amino, C₁-C₆ alkyl,C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₃-C₆ alkynyl, C₂-C₈ alkoxyalkyl, C₂-C₈haloalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈alkylsulfonylalkyl, C₂-C₈ alkylcarbonyl, C₂-C₈ haloalkylcarbonyl, C₄-C₁₀cycloalkylcarbonyl, C₂-C₈ alkoxycarbonyl, C₂-C₈ haloalkoxycarbonyl,C₄-C₁₀ cycloalkoxycarbonyl, C₂-C₈ alkylaminocarbonyl, C₃-C₁₀dialkylaminocarbonyl or C₄-C₁₀ cycloalkylaminocarbonyl; each R⁸ isindependently H, cyano or C₂-C₃ alkylcarbonyl; each R⁹ is independentlyhalogen, cyano, nitro, C₁-C₈ alkyl, C₁-C₄ cyanoalkyl, C₁-C₄ cyanoalkoxy,C₁-C₈ haloalkyl, C₁-C₈ nitroalkyl, C₂-C₈ alkenyl, C₂-C₈ haloalkenyl,C₂-C₈ nitroalkenyl, C₂-C₈ alkynyl, C₂-C₈ haloalkynyl, C₄-C₁₀cycloalkylalkyl, C₄-C₁₀ halocycloalkylalkyl, C₅-C₁₂alkylcycloalkylalkyl, C₅-C₁₂ cycloalkylalkenyl, C₅-C₁₂cycloalkylalkynyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₄-C₁₀alkylcycloalkyl, C₆-C₁₂ cycloalkylcycloalkyl, C₃-C₈ cycloalkenyl, C₃-C₈halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₂-C₈ haloalkoxyalkyl, C₃-C₈haloalkoxyalkoxy, C₁-C₄ hydroxyalkyl, C₄-C₁₀ cycloalkoxyalkyl, C₃-C₁₀alkoxyalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈alkylsulfonylalkyl, C₂-C₈ alkylaminoalkyl, C₂-C₈ haloalkylaminoalkyl,C₄-C₁₀ cycloalkylaminoalkyl, C₃-C₁₀ dialkylaminoalkyl, —CHO, C₂-C₈alkylcarbonyl, C₂-C₈ haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl,—C(═O)OH, C₂-C₈ alkoxycarbonyl, C₂-C₈ haloalkoxycarbonyl, C₄-C₁₀cycloalkoxycarbonyl, C₅-C₁₂ cycloalkylalkoxycarbonyl, —C(═O)NH₂, C₂-C₈alkylaminocarbonyl, C₄-C₁₀ cycloalkylaminocarbonyl, C₃-C₁₀dialkylaminocarbonyl, C₁-C₈ alkoxy, C₁-C₈ haloalkoxy, C₂-C₈alkoxyalkoxy, C₂-C₈ alkenyloxy, C₂-C₈ haloalkenyloxy, C₂-C₈haloalkoxyhaloalkoxy, C₃-C₈ alkynyloxy, C₃-C₈ haloalkynyloxy, C₃-C₈cycloalkoxy, C₃-C₈ halocycloalkoxy, C₄-C₁₀ cycloalkylalkoxy, C₃-C₁₀alkylcarbonylalkoxy, C₂-C₈ alkylcarbonyloxy, C₂-C₈ haloalkylcarbonyloxyor C₄-C₁₀ cycloalkylcarbonyloxy; each R¹¹ is independently halogen,cyano, nitro, C₁-C₈ alkyl, C₁-C₄ cyanoalkyl, C₁-C₄ cyanoalkoxy, C₁-C₈haloalkyl, C₁-C₈ nitroalkyl, C₂-C₈ alkenyl, C₂-C₈ haloalkenyl, C₂-C₈nitroalkenyl, C₂-C₈ alkynyl, C₂-C₈ haloalkynyl, C₄-C₁₀ cycloalkylalkyl,C₄-C₁₀ halocycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₅-C₁₂cycloalkylalkenyl, C₅-C₁₂ cycloalkylalkynyl, C₃-C₈ cycloalkyl, C₃-C₈halocycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₆-C₁₂ cycloalkylcycloalkyl,C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₂-C₈haloalkoxyalkyl, C₃-C₈ haloalkoxyalkoxy, C₁-C₄ hydroxyalkyl, C₄-C₁₀cycloalkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈alkylsulfinylalkyl, C₂-C₈ alkylsulfonylalkyl, C₂-C₈ alkylaminoalkyl,C₂-C₈ haloalkylaminoalkyl, C₄-C₁₀ cycloalkylaminoalkyl, C₃-C₁₀dialkylaminoalkyl, —CHO, C₂-C₈ alkylcarbonyl, C₂-C₈ haloalkylcarbonyl,C₄-C₁₀ cycloalkylcarbonyl, —C(═O)OH, C₂-C₈ alkoxycarbonyl, C₂-C₈haloalkoxycarbonyl, C₄-C₁₀ cycloalkoxycarbonyl, C₅-C₁₂cycloalkylalkoxycarbonyl, —C(═O)NH₂, C₂-C₈ alkylaminocarbonyl, C₄-C₁₀cycloalkylaminocarbonyl, C₃-C₁₀ dialkylaminocarbonyl, C₁-C₈ alkoxy,C₁-C₈ haloalkoxy, C₂-C₈ alkoxyalkoxy, C₂-C₈ alkenyloxy, C₂-C₈haloalkenyloxy, C₂-C₈ haloalkoxyhaloalkoxy, C₃-C₈ alkynyloxy, C₃-C₈haloalkynyloxy, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₄-C₁₀cycloalkylalkoxy, C₃-C₁₀ alkylcarbonylalkoxy, C₂-C₈ alkylcarbonyloxy,C₂-C₈ haloalkylcarbonyloxy, C₄-C₁₀ cycloalkylcarbonyloxy, C₁-C₈alkylsulfonyloxy, C₁-C₈ haloalkylsulfonyloxy, C₁-C₈ alkylthio, C₁-C₈haloalkylthio, C₃-C₈ cycloalkylthio, C₁-C₈ alkylsulfinyl, C₁-C₈haloalkylsulfinyl, C₁-C₈ alkylsulfonyl, C₁-C₈ haloalkylsulfonyl, C₃-C₈cycloalkylsulfonyl, formylamino, C₂-C₈ alkylcarbonylamino, C₂-C₈haloalkylcarbonylamino or C₂-C₈ alkoxycarbonylamino; and each R¹⁰ andR¹² is independently C₁-C₃ alkyl, C₃-C₆ cycloalkyl, C₂-C₃ alkoxyalkyl,C₂-C₃ alkylcarbonyl, C₂-C₃ alkoxycarbonyl or C₂-C₃ alkylaminoalkyl. 3.The compound of claim 2 wherein Q¹ is a phenyl ring optionallysubstituted with up to 5 substituents independently selected from R⁹; ora 5- to 6-membered fully unsaturated heterocyclic ring, each ringcontaining ring members selected from carbon atoms and 1 to 4heteroatoms independently selected from up to 2 O, up to 2 S and up to 4N atoms, wherein up to 3 carbon ring members are independently selectedfrom C(═O) and C(═S), and the sulfur atom ring members are independentlyselected from S(═O)_(u)(═NR⁸)_(v), each ring optionally substituted withup to 5 substituents independently selected from R⁹ on carbon atom ringmembers and selected from R¹⁰ on nitrogen atom ring members; Q² is aphenyl ring optionally substituted with up to 5 substituentsindependently selected from R¹¹; R¹ and R² are each independently H, Cl,or CH₃; Y is O; A is a saturated or partially unsaturated chaincontaining 2 to 4 atoms selected from up to 2 carbon and up to 1 Natoms, wherein up to 1 carbon member is independently selected fromC(═O) and C(═S); the said chain optionally substituted with up to 2substituents independently selected from R³ on carbon atoms and R⁴ onnitrogen atoms; each R³ is independently cyano, —CO₂H, C₁-C₄ alkyl,C₁-C₄ haloalkyl, C₁-C₄ alkylthio or C₄-C₆ cycloalkylalkyl; each R⁴ isindependently C₁-C₄ alkyl; J is —CR⁵R⁶—; R⁵ and R⁶ are eachindependently H or halogen; R⁷ is H, hydroxy, amino, C₁-C₆ alkyl, C₁-C₆haloalkyl, C₂-C₆ alkenyl, C₃-C₆ alkynyl, C₂-C₈ alkoxyalkyl, C₂-C₈haloalkoxyalkyl or C₂-C₈ alkylthioalkyl; each R⁸ is independently H;each R⁹ is independently halogen, cyano, nitro, C₁-C₈ alkyl, C₁-C₄cyanoalkyl, C₁-C₄ cyanoalkoxy, C₁-C₈ haloalkyl, C₁-C₈ nitroalkyl, C₂-C₈alkenyl, C₂-C₈ haloalkenyl, C₂-C₈ nitroalkenyl, C₂-C₈ alkynyl, C₂-C₈haloalkynyl, C₄-C₁₀ cycloalkylalkyl, C₄-C₁₀ halocycloalkylalkyl, C₅-C₁₂alkylcycloalkylalkyl, C₅-C₁₂ cycloalkylalkenyl, C₅-C₁₂cycloalkylalkynyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₄-C₁₀alkylcycloalkyl, C₆-C₁₂ cycloalkylcycloalkyl, C₃-C₈ cycloalkenyl, C₃-C₈halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₂-C₈ haloalkoxyalkyl, C₃-C₈haloalkoxyalkoxy, C₁-C₄ hydroxyalkyl, C₄-C₁₀ cycloalkoxyalkyl, C₃-C₁₀alkoxyalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈alkylsulfonylalkyl, C₂-C₈ alkylaminoalkyl, C₂-C₈ haloalkylaminoalkyl,C₄-C₁₀ cycloalkylaminoalkyl or C₃-C₁₀ dialkylaminoalkyl; each R¹¹ isindependently halogen, cyano, nitro, C₁-C₈ alkyl, C₁-C₄ cyanoalkyl,C₁-C₄ cyanoalkoxy, C₁-C₈ haloalkyl, C₁-C₈ nitroalkyl, C₂-C₈ alkenyl,C₂-C₈ haloalkenyl, C₂-C₈ nitroalkenyl, C₂-C₈ alkynyl, C₂-C₈ haloalkynyl,C₄-C₁₀ cycloalkylalkyl, C₄-C₁₀ halocycloalkylalkyl, C₅-C₁₂alkylcycloalkylalkyl, C₅-C₁₂ cycloalkylalkenyl, C₅-C₁₂cycloalkylalkynyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₄-C₁₀alkylcycloalkyl, C₆-C₁₂ cycloalkylcycloalkyl, C₃-C₈ cycloalkenyl, C₃-C₈halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₂-C₈ haloalkoxyalkyl, C₃-C₈haloalkoxyalkoxy, C₁-C₄ hydroxyalkyl, C₄-C₁₀ cycloalkoxyalkyl, C₃-C₁₀alkoxyalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈alkylsulfonylalkyl, C₁-C₈ alkylsulfonyloxy, C₁-C₈ haloalkylsulfonyloxy,C₁-C₈ alkylthio, C₁-C₈ haloalkylthio, C₃-C₈ cycloalkylthio, C₁-C₈alkylsulfinyl, C₁-C₈ haloalkylsulfinyl, C₁-C₈ alkylsulfonyl, C₁-C₈haloalkylsulfonyl or C₃-C₈ cycloalkylsulfonyl; and each R¹⁰ and R¹² isindependently C₁-C₃ alkyl, C₃-C₆ cycloalkyl or C₂-C₃ alkoxyalkyl.
 4. Thecompound of claim 3 wherein Q¹ is a phenyl ring optionally substitutedwith up to 5 substituents independently selected from R⁹; Q² is a phenylring optionally substituted with up to 3 substituents independentlyselected from R¹¹; R¹ and R² are each independently H or Cl; A is asaturated or partially unsaturated chain containing 2 to 3 atomsselected from up to 2 carbon and up to 1 N atoms, wherein up to 1 carbonmember is independently selected from C(═O); the said chain optionallysubstituted with up to 1 substituent independently selected from R³ oncarbon atoms and R⁴ on nitrogen atoms; each R³ is independently cyano,—CO₂H or C₁-C₄ alkyl; each R⁴ is CH₃; R⁵ and R⁶ are each independently Hor halogen; R⁷ is H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₃-C₆ alkynyl or C₂-C₈alkoxyalkyl each R⁹ is independently halogen, cyano, nitro, C₁-C₈ alkyl,C₁-C₄ cyanoalkyl, C₁-C₄ cyanoalkoxy, C₁-C₈ haloalkyl, C₁-C₈ nitroalkyl,C₂-C₈ alkenyl, C₂-C₈ haloalkenyl, C₂-C₈ nitroalkenyl, C₂-C₈ alkynyl,C₂-C₈ haloalkynyl, C₄-C₁₀ cycloalkylalkyl, C₄-C₁₀ halocycloalkylalkyl,C₅-C₁₂ alkylcycloalkylalkyl, C₅-C₁₂ cycloalkylalkenyl, C₅-C₁₂cycloalkylalkynyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₄-C₁₀alkylcycloalkyl or C₆-C₁₂ cycloalkylcycloalkyl; and each R¹¹ isindependently halogen, cyano, nitro, C₁-C₈ alkyl, C₁-C₄ cyanoalkyl,C₁-C₄ cyanoalkoxy, C₁-C₈ haloalkyl, C₁-C₈ nitroalkyl, C₂-C₈ alkenyl,C₂-C₈ haloalkenyl, C₂-C₈ nitroalkenyl, C₂-C₈ alkynyl, C₂-C₈ haloalkynyl,C₄-C₁₀ cycloalkylalkyl, C₄-C₁₀ halocycloalkylalkyl, C₅-C₁₂alkylcycloalkylalkyl, C₅-C₁₂ cycloalkylalkenyl, C₅-C₁₂cycloalkylalkynyl, C₃-C₈ cycloalkyl, C₁-C₈ alkylsulfonyl, C₁-C₈haloalkylsulfonyl or C₃-C₈ cycloalkylsulfonyl.
 5. The compound of claim4 wherein Q¹ is a phenyl ring substituted with 1 to 3 substituentsindependently selected from R⁹; Q² is a phenyl ring substituted with 1substituent independently selected from R¹¹ at the 3-position; R¹ and R²are each H; A is —CH₂CH₂CH₂—, —CH₂N—, —C(═O)CH₂— or —CH═CH— wherein thebond projecting to the left is connected to nitrogen of the —N-J-moiety, and the bond projecting to the right is connected to thenitrogen of the —N═C— moiety of Formula 1; each R⁹ is independentlyhalogen, cyano, nitro, C₁-C₈ alkyl, C₁-C₄ cyanoalkyl, C₁-C₄ cyanoalkoxyor C₁-C₈ haloalkyl; and each R¹¹ is independently halogen, C₁-C₈ alkyl,C₁-C₈ haloalkyl or C₁-C₈ alkylsulfonyl.
 6. The compound of claim 5wherein Q¹ is a phenyl ring substituted with 1 to 2 substituentsindependently selected from R⁹; A is —CH₂CH₂CH₂—; each R⁹ isindependently halogen or C₁-C₈ haloalkyl; and each R¹¹ is independentlyF, Cl, CH₃, CF₃ or —SO₂CF₃.
 7. The compound of claim 5 wherein Q¹ is aphenyl ring substituted with 1 to 2 substituents independently selectedfrom R⁹; A is —NCH₂— wherein the bond projecting to the left isconnected to nitrogen of the —N-J- moiety, and the bond projecting tothe right is connected to the nitrogen of the —N═C— moiety of Formula 1;each R⁹ is independently F, Cl, CF₃; and each R¹¹ is independently F,Cl, CH₃, CF₃ or —SO₂CF₃.
 8. A compound of claim 1 selected from thegroup consisting ofN-(2-fluorophenyl)-6,7-dihydro-6-[3-(trifluoromethyl)phenyl]-5H-pyrrolo[2,1-c]-1,2,4-triazole-7-carboxamide;andN-(2-fluorophenyl)-2,3,7-tetrahydro-3-oxo-6-[3-(trifluoromethyl)pheny]-5H-pyrrolo[1,2-a]imidazole-7-carboxamide.9. A compound of claim 4 wherein A is —CH₂CH₂CH₂—, —CH═N—, —C(CH₃)═N—,—C(CH₂CH₃)═N—, C(CH₂CH₂CH₃)═N—, —C(CF₃)═N—, —C(═O)CH₂— or —CH═CH—wherein the bond projecting to the left is connected to nitrogen of the—N-J- moiety, and the bond projecting to the right is connected to thenitrogen of the —N═C— or —N—CH— moiety of Formula 1; each R⁹ isindependently halogen, cyano, nitro, C₁-C₈ alkyl, C₁-C₄ cyanoalkyl,C₁-C₄ cyanoalkoxy or C₁-C₈ haloalkyl; and each R¹¹ is independentlyhalogen, C₁-C₈ alkyl, C₁-C₈ haloalkyl or C₁-C₈ alkylsulfonyl.
 10. Acompound of claim 9 wherein A is —CH═N—, —C(CH₃)═N—, —C(CH₂CH₃)═N—,—C(CH₂CH₂CH₃)═N— or C(CF₃)═N— wherein the bond projecting to the left isconnected to nitrogen of the —N-J- moiety, and the bond projecting tothe right is connected to the nitrogen of the —N═C— or —N—CH— moiety ofFormula 1; each R⁹ is independently halogen, C₁-C₈ alkyl or C₁-C₈haloalkyl; and each R¹¹ is independently F, Cl, CH₃ or CF₃.
 11. Aherbicidal composition comprising a compound of claim 1 and at least onecomponent selected from the group consisting of surfactants, soliddiluents and liquid diluents.
 12. A herbicidal composition comprising acompound of claim 1, an active ingredient selected from the groupconsisting of herbicides and herbicide safeners, and at least onecomponent selected from the group consisting of surfactants, soliddiluents and liquid diluents.
 13. A herbicidal mixture comprising (a) acompound of claim 1, and (b) at least one active ingredient selectedfrom (b1) photosystem II inhibitors, (b2) acetohydroxy acid synthase(AHAS) inhibitors, (b3) acetyl-CoA carboxylase (ACCase) inhibitors, (b4)auxin mimics, (b5) 5-enol-pyruvylshikimate-3-phosphate (EPSP) synthaseinhibitors, (b6) photosystem I electron diverters, (b7)protoporphyrinogen oxidase (PPO) inhibitors, (b8) glutamine synthetase(GS) inhibitors, (b9) very long chain fatty acid (VLCFA) elongaseinhibitors, (b10) auxin transport inhibitors, (b11) phytoene desaturase(PDS) inhibitors, (b12) 4-hydroxyphenyl-pyruvate dioxygenase (HPPD)inhibitors, (b13) homogentisate solenesyltransererase (HST) inhibitors,(b14) cellulose biosynthesis inhibitors, (b15) other herbicidesincluding mitotic disruptors, organic arsenicals, asulam, bromobutide,cinmethylin, cumyluron, dazomet, difenzoquat, dymron, etobenzanid,flurenol, fosamine, fosamine-ammonium, hydantocidin, metam,methyldymron, oleic acid, oxaziclomefone, pelargonic acid andpyributicarb, and (b16) herbicide safeners; and salts of compounds of(b1) through (b16).
 14. A method for controlling the growth of undesiredvegetation comprising contacting the vegetation or its environment witha herbicidally effective amount of a compound of claim 1.